Biggest changeWe have until October 15, 2023 to file our U.S. federal income tax return for the year ended December 31, 2022. 75 The following table reflects the cash distributions, including distributions reinvested, if any, per share that we have paid on our common stock since the beginning of the 2020 fiscal year through 2022: Date Declared Record Date Payment Date Total Distributions GAAP net investment income Distributions in excess of/ (less than) GAAP net investment income (1) Fiscal 2022 July 21, 2022 December 16, 2022 December 30, 2022 $ 0.035 $ N/A $ — July 21, 2022 November 16, 2022 November 30, 2022 0.035 N/A — July 21, 2022 October 17, 2022 October 31, 2022 0.035 N/A — Total (Fourth Quarter 2022) 0.105 0.13 (0.03 ) April 21, 2022 September 16, 2022 September 30, 2022 $ 0.035 $ N/A $ — April 21, 2022 August 17, 2022 August 31, 2022 0.035 N/A — April 21, 2022 July 15, 2022 July 29, 2022 0.035 N/A — Total (Third Quarter 2022) 0.105 0.11 (0.01 ) March 1, 2022 June 16, 2022 June 30, 2022 $ 0.035 $ N/A $ — March 1, 2022 May 17, 2022 May 31, 2022 0.035 N/A — March 1, 2022 April 15, 2022 April 29, 2022 0.035 N/A — Total (Second Quarter 2022) 0.105 0.09 0.02 October 22, 2021 March 17, 2022 March 31, 2022 $ 0.035 $ N/A $ — October 22, 2021 February 14, 2022 February 28, 2022 0.035 N/A — October 22, 2021 January 17, 2022 January 31, 2022 0.035 N/A — Total (First Quarter 2022) 0.105 0.09 0.02 Total (2022) $ 0.420 (1) $ 0.42 $ — Fiscal 2021 July 22, 2021 December 17, 2021 December 31, 2021 $ 0.035 $ N/A $ — July 22, 2021 November 16, 2021 November 30, 2021 0.035 N/A — July 22, 2021 October 15, 2021 October 29, 2021 0.035 N/A — Total (Fourth Quarter 2021) 0.105 0.09 0.02 April 22, 2021 September 16, 2021 September 30, 2021 $ 0.035 $ N/A $ — April 22, 2021 August 17, 2021 August 31, 2021 0.035 N/A — April 22, 2021 July 16, 2021 July 30, 2021 0.035 N/A — Total (Third Quarter 2021) 0.105 0.08 0.02 February 23, 2021 June 16, 2021 June 30, 2021 $ 0.035 $ N/A $ — February 23, 2021 May 14, 2021 May 28, 2021 0.035 N/A — February 23, 2021 April 16, 2021 April 30, 2021 0.035 N/A — Total (Second Quarter 2021) 0.105 0.06 0.05 October 22, 2020 March 17, 2021 March 31, 2021 $ 0.035 $ N/A $ — October 22, 2020 February 12, 2021 February 26, 2021 0.035 N/A — October 22, 2020 January 15, 2021 January 29, 2021 0.035 N/A — Total (First Quarter 2021) 0.105 0.10 — Total (2021) $ 0.420 (2) $ 0.32 (4) $ 0.10 (4) Fiscal 2020 September 11, 2020 December 16, 2020 December 31, 2020 $ 0.035 $ N/A $ — September 11, 2020 November 13, 2020 November 30, 2020 0.035 N/A — September 11, 2020 October 16, 2020 October 30, 2020 0.035 N/A — Total (Fourth Quarter 2020) 0.105 0.10 — June 1, 2020 September 16, 2020 September 30, 2020 $ 0.035 $ N/A $ — June 1, 2020 August 17, 2020 August 31, 2020 0.035 N/A — June 1, 2020 July 17, 2020 July 31, 2020 0.035 N/A — Total (Third Quarter 2020) 0.105 0.09 0.01 February 24, 2020 June 15, 2020 June 30, 2020 $ 0.067 $ N/A $ — February 24, 2020 May 14, 2020 May 29, 2020 0.067 N/A — February 24, 2020 April 15, 2020 April 30, 2020 0.067 N/A — Total (Second Quarter 2020) 0.201 0.09 0.11 October 25, 2019 March 17, 2020 March 31, 2020 $ 0.067 $ N/A $ — October 25, 2019 February 14, 2020 February 28, 2020 0.067 N/A — October 25, 2019 January 17, 2020 January 31, 2020 0.067 N/A — Total (First Quarter 2020) 0.201 0.13 0.07 Total (2020) $ 0.612 (3) $ 0.40 (4) $ 0.21 (4) 76 ____________ (1) The tax characterization of cash distributions for the year ended December 31, 2022 will not be known until the tax return for such year is finalized.
Biggest changeWe have until October 15, 2024 to file our U.S. federal income tax return for the year ended December 31, 2023. 76 The following table reflects the cash distributions, including distributions reinvested, if any, per share that we have paid on our common stock since the beginning of the 2021 fiscal year through 2023: Date Declared Record Date Payment Date Total Distributions GAAP Net Investment Income Distributions in Excess of/ (Less than) GAAP Net Investment Income (1) Fiscal 2023 August 3, 2023 December 15, 2023 December 29, 2023 $ 0.035 $ N/A $ — August 3, 2023 November 16, 2023 November 30, 2023 0.035 N/A — August 3, 2023 October 17, 2023 October 31, 2023 0.035 N/A — Total (Fourth Quarter 2023) 0.105 0.13 (0.03 ) August 3, 2023 (5) September 15, 2023 September 29, 2023 $ 0.120 $ N/A $ — April 25, 2023 September 15, 2023 September 29, 2023 0.035 N/A — April 25, 2023 August 17, 2023 August 31, 2023 0.035 N/A — April 25, 2023 July 17, 2023 July 31, 2023 0.035 N/A — Total (Third Quarter 2023) 0.225 0.11 0.12 March 16, 2023 June 16, 2023 June 30, 2023 $ 0.035 $ N/A $ — March 16, 2023 May 17, 2023 May 31, 2023 0.035 N/A — March 16, 2023 April 14, 2023 April 28, 2023 0.035 N/A — Total (Second Quarter 2023) 0.105 0.13 (0.03 ) October 20, 2022 March 17, 2023 March 31, 2023 $ 0.035 $ N/A $ — October 20, 2022 February 14, 2023 February 28, 2023 0.035 N/A — October 20, 2022 January 17, 2023 January 31, 2023 0.035 N/A — Total (First Quarter 2023) 0.105 0.13 (0.03 ) Total (2023) $ 0.540 (1) $ 0.51 (4) $ 0.03 (4) Fiscal 2022 July 21, 2022 December 16, 2022 December 30, 2022 $ 0.035 $ N/A $ — July 21, 2022 November 16, 2022 November 30, 2022 0.035 N/A — July 21, 2022 October 17, 2022 October 31, 2022 0.035 N/A — Total (Fourth Quarter 2022) 0.105 0.13 (0.03 ) April 21, 2022 September 16, 2022 September 30, 2022 $ 0.035 $ N/A $ — April 21, 2022 August 17, 2022 August 31, 2022 0.035 N/A — April 21, 2022 July 15, 2022 July 29, 2022 0.035 N/A — Total (Third Quarter 2022) 0.105 0.11 (0.01 ) March 1, 2022 June 16, 2022 June 30, 2022 $ 0.035 $ N/A $ — March 1, 2022 May 17, 2022 May 31, 2022 0.035 N/A — March 1, 2022 April 15, 2022 April 29, 2022 0.035 N/A — Total (Second Quarter 2022) 0.105 0.09 0.02 October 22, 2021 March 17, 2022 March 31, 2022 $ 0.035 $ N/A $ — October 22, 2021 February 14, 2022 February 28, 2022 0.035 N/A — October 22, 2021 January 17, 2022 January 31, 2022 0.035 N/A — Total (First Quarter 2022) 0.105 0.09 0.02 Total (2022) $ 0.420 (2) $ 0.42 $ — Fiscal 2021 July 22, 2021 December 17, 2021 December 31, 2021 $ 0.035 $ N/A $ — July 22, 2021 November 16, 2021 November 30, 2021 0.035 N/A — July 22, 2021 October 15, 2021 October 29, 2021 0.035 N/A — Total (Fourth Quarter 2021) 0.105 0.09 0.02 April 22, 2021 September 16, 2021 September 30, 2021 $ 0.035 $ N/A $ — April 22, 2021 August 17, 2021 August 31, 2021 0.035 N/A — April 22, 2021 July 16, 2021 July 30, 2021 0.035 N/A — Total (Third Quarter 2021) 0.105 0.08 0.02 February 23, 2021 June 16, 2021 June 30, 2021 $ 0.035 $ N/A $ — February 23, 2021 May 14, 2021 May 28, 2021 0.035 N/A — February 23, 2021 April 16, 2021 April 30, 2021 0.035 N/A — Total (Second Quarter 2021) 0.105 0.06 0.05 October 22, 2020 March 17, 2021 March 31, 2021 $ 0.035 $ N/A $ — October 22, 2020 February 12, 2021 February 26, 2021 0.035 N/A — October 22, 2020 January 15, 2021 January 29, 2021 0.035 N/A — Total (First Quarter 2021) 0.105 0.10 — Total (2021) $ 0.420 (3) $ 0.32 (4) $ 0.10 (4) 77 ____________ (1) The tax characterization of cash distributions for the year ended December 31, 2023 will not be known until the tax return for such year is finalized.
Subject to satisfaction of certain conditions to the Order, the Company and certain of its affiliates are now permitted, together with any future BDCs, registered closed -end funds and certain private funds, each of whose investment adviser is the Company’s investment adviser or an investment adviser controlling, controlled by, or under common control with the Company’s investment adviser, to co -invest in negotiated investment opportunities where doing so would otherwise be prohibited under the 1940 Act, providing 77 the Company’s stockholders with access to a broader array of investment opportunities.
Subject to satisfaction of certain conditions to the Order, the Company and certain of its affiliates are now permitted, together with any future BDCs, registered closed -end funds and certain private funds, each of whose investment adviser is the Company’s investment adviser or an investment adviser controlling, controlled by, or under common control with the Company’s investment adviser, to co -invest in negotiated investment opportunities where doing so would otherwise be prohibited under the 1940 Act, providing the Company’s stockholders with access to a broader array of investment opportunities.
This includes net unrealized appreciation of approximately $20.4 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $37.3 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $17.0 million.
This includes net unrealized 73 appreciation of approximately $20.4 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $37.3 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $17.0 million.
The forward -looking statements contained in this Annual Report on Form 10 -K involve risks and uncertainties, including statements as to: • our future operating results, including our ability to achieve objectives; • our business prospects and the prospects of our portfolio companies; • the impact of investments that we expect to make; • our contractual arrangements and relationships with third parties; • the dependence of our future success on the general economy and its impact on the industries in which we invest; • the ability of our portfolio companies and CLO investments to achieve their objectives; 63 • the valuation of our investments in portfolio companies and CLOs, particularly those having no liquid trading market; • market conditions and our ability to access alternative debt markets and additional debt and equity capital; • our expected financings and investments; • the adequacy of our cash resources and working capital; • the timing of cash flows, if any, from the operations of our portfolio companies and CLO investments; and • the ability of our investment adviser to locate suitable investments for us and monitor and administer our investments .
The forward -looking statements contained in this Annual Report on Form 10 -K involve risks and uncertainties, including statements as to: • our future operating results, including our ability to achieve objectives; • our business prospects and the prospects of our portfolio companies; • the impact of investments that we expect to make; • our contractual arrangements and relationships with third parties; • the dependence of our future success on the general economy and its impact on the industries in which we invest; • the ability of our portfolio companies and CLO investments to achieve their objectives; 64 • the valuation of our investments in portfolio companies and CLOs, particularly those having no liquid trading market; • market conditions and our ability to access alternative debt markets and additional debt and equity capital; • our expected financings and investments; • the adequacy of our cash resources and working capital; • the timing of cash flows, if any, from the operations of our portfolio companies and CLO investments; and • the ability of our investment adviser to locate suitable investments for us and monitor and administer our investments.
The components of the net change in unrealized depreciation during the year ended December 31, 2022 were as follows ($ in millions): Portfolio Company Changes in unrealized depreciation ConvergeOne Holdings, Inc. $ (10.3 ) Quest Software, Inc. (8.3 ) Sound Point CLO XVI, Ltd. (7.6 ) Octagon Investment Partners 49, Ltd.
The components of the net change in unrealized appreciation/depreciation during the year ended December 31, 2022 were as follows ($ in millions): Portfolio Company Changes in Unrealized Depreciation ConvergeOne Holdings, Inc. $ (10.3 ) Quest Software, Inc. (8.3 ) Sound Point CLO XVI, Ltd. (7.6 ) Octagon Investment Partners 49, Ltd.
Cohen and Rosenthal currently serve as Chief Executive Officer and President, respectively, of Oxford Lane Capital Corp., a non -diversified closed -end management investment company that invests primarily in equity and junior debt tranches of CLO vehicles, and its investment adviser, Oxford Lane Management, LLC.
Cohen and Rosenthal currently serve as Chief Executive Officer and President, respectively, of Oxford Lane Capital Corp., a non -diversified closed -end management investment company that invests primarily in equity and junior debt tranches of CLO vehicles, and its investment adviser, Oxford Lane Management.
Oxford Funds provides Oxford Lane Capital Corp. with office facilities and administrative services pursuant to an administration agreement and also serves as the managing member of Oxford Lane Management, LLC. In addition, Bruce L.
Oxford Funds provides Oxford Lane Capital Corp. with office facilities and administrative services pursuant to an administration agreement and also serves as the managing member of Oxford Lane Management. In addition, Bruce L.
Related Party Transactions” in the notes to our financial statements. 71 The expense attributable to the capital gains incentive fee, as reported under GAAP, is calculated as if the Company’s entire portfolio had been liquidated at period end, and therefore is calculated on the basis of net realized and unrealized gains and losses at the end of each period.
Related Party Transactions” in the notes to our financial statements. 72 The expense attributable to the capital gains incentive fee, as reported under GAAP, is calculated as if the Company’s entire portfolio had been liquidated at period end, and therefore is calculated on the basis of net realized and unrealized gains and losses at the end of each period.
The actual amounts and sources of the amounts for tax reporting purposes will depend upon the Company’s investment performance and may be subject to change based on tax regulations. (2) Cash distributions for the year ended December 31, 2021 represented 100% net investment income and therefore there was no tax return of capital.
The actual amounts and sources of the amounts for tax reporting purposes will depend upon the Company’s investment performance and may be subject to change based on tax regulations. (2) Cash distributions for the year ended December 31, 2022 represented 100% net investment income and therefore there was no tax return of capital.
The weighted average annualized yield was computed using the effective interest rates as of December 31, 2022, including accretion of OID and excluding any debt investments on non -accrual status. There can be no assurance that the weighted average annualized yield will remain at its current level.
The weighted average annualized yield was computed using the effective interest rates as of December 31, 2023, including accretion of OID and excluding any debt investments on non -accrual status. There can be no assurance that the weighted average annualized yield will remain at its current level.
(2) Totals may not sum due to rounding. The following tables present the top ten industries (based upon Moody’s industry classifications) of the aggregate holdings of the CLOs included in our portfolio, based on par value, as of December 31, 2022 and December 31, 2021.
(2) Totals may not sum due to rounding. The following tables present the top ten industries (based upon Moody’s industry classifications) of the aggregate holdings of the CLOs included in our portfolio, based on par value, as of December 31, 2023 and December 31, 2022.
The following analysis of our financial condition and results of operations should be read in conjunction with our financial statements and the related notes thereto contained elsewhere in this Form 10 -K . 64 OVERVIEW Our investment objective is to maximize our portfolio’s total return.
The following analysis of our financial condition and results of operations should be read in conjunction with our financial statements and the related notes thereto contained elsewhere in this Form 10 -K . 65 OVERVIEW Our investment objective is to maximize our portfolio’s total return.
Estimates made in the preparation of our financial statements include the valuation of investments and the related amounts of unrealized appreciation and depreciation of investments recorded. We believe that there is no single definitive method for determining fair value in good faith.
Estimates made in the preparation of our financial statements include the valuation of investments and the related amounts of unrealized appreciation and depreciation of investments recorded. We believe that there is no single definitive method for determining fair value.
On June 14, 2017, the Securities and Exchange Commission issued an order permitting the Company and certain of its affiliates to complete negotiated co -investment transactions in portfolio companies, subject to certain conditions (the “Order”).
On June 14, 2017, the Securities and Exchange Commission issued the Order permitting the Company and certain of its affiliates to complete negotiated co -investment transactions in portfolio companies, subject to certain conditions.
ASC 820 -10 clarified the definition of fair value and requires companies to expand their disclosure about the use of fair value to measure assets and liabilities in interim and annual periods subsequent to initial recognition.
ASC 820 -10 clarifies the definition of fair value and requires companies to expand their disclosure about the use of fair value to measure assets and liabilities in interim and annual periods subsequent to initial recognition.
For the years ended December 31, 2022 and 2021, no accrual was required as a result of the impact of accumulated net unrealized depreciation and net realized losses on our portfolio.
For the years ended December 31, 2023 and 2022, no accrual was required as a result of the impact of accumulated net unrealized depreciation and net realized losses on our portfolio.
The final determination of the source of all distributions in 2022 will be made after year -end and the amounts represented may be materially different from the amounts disclosed in the final Form 1099 -DIV notice.
The final determination of the source of all distributions in 2023 will be made after year -end and the amounts represented may be materially different from the amounts disclosed in the final Form 1099 -DIV notice.
For information regarding results of operations for the year ended December 31, 2020, refer to Part II Item 7 in our Form 10 -K for the year ended December 31, 2021, as filed with the SEC on March 7, 2022, which is incorporated by reference herein.
For information regarding results of operations for the year ended December 31, 2021, refer to Part II Item 7 in our Form 10 -K for the year ended December 31, 2022, as filed with the SEC on March 23, 2023, which is incorporated by reference herein.
For the year ended December 31, 2022, the amounts and sources of distributions reported are only estimates and are not being provided for U.S. tax reporting purposes.
For the year ended December 31, 2023, the amounts and sources of distributions reported are only estimates and are not being provided for U.S. tax reporting purposes.
We consider the attributes of current market conditions on an on -going basis and 78 have determined that due to the general illiquidity of the market for its investment portfolio, whereby little or no market data exists, substantially all of our fair valued investments are measured based upon Level 3 inputs as of December 31, 2022 and 2021.
We consider the attributes of current market conditions on an on -going basis and have determined that due to the general illiquidity of the market for our investment portfolio, whereby little or no market data exists, substantially all of our fair valued investments are measured based upon Level 3 inputs as of December 31, 2023 and December 31, 2022.
Rubin serves as the Chief Financial Officer, Treasurer and Corporate Secretary of Oxford Lane Capital Corp. and Chief Financial Officer and Treasurer of Oxford Lane Management, LLC, and Mr. Cummins serves as the Chief Compliance Officer of Oxford Lane Capital Corp. and Oxford Lane Management, LLC.
Rubin serves as the Chief Financial Officer, Treasurer and Corporate Secretary of Oxford Lane Capital Corp. and Chief Financial Officer and Treasurer of Oxford Lane Management, and Mr. Cummins serves as the Chief Compliance Officer of Oxford Lane Capital Corp. and Oxford Lane Management. • Messrs.
CRITICAL ACCOUNTING POLICIES The preparation of financial statements and related disclosures in conformity with generally accepted accounting principles in the United States (“GAAP”) requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the financial statements, and revenues and expenses during the periods reported.
CRITICAL ACCOUNTING ESTIMATES The preparation of financial statements and related disclosures in conformity with generally accepted accounting principles in the United States (“GAAP”) requires management to make estimates and assumptions that affect (i) the reported amounts of assets and liabilities, (ii) disclosure of contingent assets and liabilities at the date of the financial statements, and (iii) revenues and expenses during the periods reported.
We also engage third -party valuation firms to provide assistance in valuing certain of its syndicated loans and bilateral investments, including related equity investments, although our Board of Directors ultimately determines the appropriate valuation of each such investment. Changes in fair value, as described above, are recorded in the statements of operations as net change in unrealized appreciation/depreciation.
We may also engage a third -party valuation firm to provide assistance in valuing certain of our syndicated loans and bilateral investments, including related equity investments, although our Board of Directors ultimately determines the appropriate valuation of each such investment. Changes in fair value, as described above, are recorded in the statements of operations as net change in unrealized appreciation/depreciation.
For the year ended December 31, 2022, the net decrease in net assets resulting from operations per common share was $1.72 (basic and diluted), compared to a net increase in net assets per common share of $0.80 (basic and diluted) for the year ended December 31, 2021, based on the weighted average common shares outstanding for the respective periods.
For the year ended December 31, 2023, the net increase in net assets resulting from operations per common share was $0.32 (basic and diluted), compared to a net decrease in net assets per common share of $1.72 (basic and diluted) for the year ended December 31, 2022, based on the weighted average common shares outstanding for the respective periods.
As a result, certain conflicts of interest may arise with respect to the management of our portfolio by Messrs. Cohen and Rosenthal on the one hand, and the obligations of Messrs. Cohen and Rosenthal to manage Oxford Lane Capital Corp., Oxford Bridge II, LLC and the Oxford Gate Funds, respectively, on the other hand.
As a result, certain conflicts of interest may arise with respect to the management of our portfolio by Messrs. Cohen and Rosenthal on the one hand, and the obligations of Messrs. Cohen and Rosenthal to manage Oxford Lane Capital Corp., Oxford Park Income Fund, Inc., Oxford Bridge II, LLC and the Oxford Gate Funds, respectively, on the other hand.
The aggregate accrued interest which remained payable as of December 31, 2022 and 2021, was approximately $1.2 million.
The aggregate accrued interest which remained payable as of December 31, 2023 and 2022, was approximately $1.2 million.
The number and amount of investments included in Grade 3, 4 or 5 may fluctuate from year to year. 69 RESULTS OF OPERATIONS Set forth below is a comparison of our results of operations for the years ended December 31, 2022 and 2021.
The number and amount of investments included in Grade 3, 4 or 5 may fluctuate from year to year. 70 RESULTS OF OPERATIONS Set forth below is a comparison of our results of operations for the years ended December 31, 2023 and 2022.
Refer to the table below, which reconciles the investment portfolio for the year ended December 31, 2022 and the year ended December 31, 2021.
Refer to the table below, which reconciles the investment portfolio for the year ended December 31, 2023 and the year ended December 31, 2022.
As of December 31, 2022, our asset coverage for borrowed amounts was approximately 171%. As of December 31, 2021, our asset coverage for borrowed amounts was approximately 227%. The following are our outstanding principal amounts, carrying values and fair values of our borrowings as of December 31, 2022 and December 31, 2021.
As of December 31, 2022, our asset coverage for borrowed amounts was approximately 171%. The following are our outstanding principal amounts, carrying values and fair values of our borrowings as of December 31, 2023 and December 31, 2022.
Top Ten Industries December 31, 2022 High Tech Industries 10.1 % Healthcare & Pharmaceuticals 9.8 % Banking, Finance, Insurance & Real Estate 9.6 % Business Services 8.8 % Media: Broadcasting & Subscription 5.0 % Telecommunications 4.8 % Hotels, Gaming & Leisure 4.7 % Chemicals, Plastics & Rubber 4.5 % Beverage, Food & Tobacco 3.7 % Construction & Building 3.6 % Total 64.6 % Top Ten Industries December 31, 2021 Healthcare & Pharmaceuticals 9.9 % Banking, Finance, Insurance & Real Estate 9.7 % High Tech Industries 9.5 % Business Services 8.4 % Hotels, Gaming & Leisure 5.2 % Media: Broadcasting & Subscription 5.0 % Telecommunications 4.6 % Chemicals, Plastics & Rubber 4.1 % Beverage, Food & Tobacco 3.8 % Construction & Building 3.6 % Total 63.8 % 68 PORTFOLIO GRADING We have adopted a credit grading system to monitor the quality of our debt investment portfolio.
Top Ten Industries December 31, 2023 High tech industries 11.3 % Healthcare & pharmaceuticals 10.1 % Banking, finance, insurance & real estate 9.9 % Business services 9.4 % Media: broadcasting & subscription 5.6 % Telecommunications 4.9 % Hotels, gaming & leisure 4.4 % Chemicals, plastics & rubber 3.9 % Beverage, food & tobacco 3.7 % Construction & building 3.5 % Total 66.7 % Top Ten Industries December 31, 2022 High tech industries 10.1 % Healthcare & pharmaceuticals 9.8 % Banking, finance, insurance & real estate 9.6 % Business services 8.8 % Media: broadcasting & subscription 5.0 % Telecommunications 4.8 % Hotels, gaming & leisure 4.7 % Chemicals, plastics & rubber 4.5 % Beverage, food & tobacco 3.7 % Construction & building 3.6 % Total 64.6 % 69 PORTFOLIO GRADING We have adopted a credit grading system to monitor the quality of our debt investment portfolio.
If we do not distribute a certain percentage of our income annually, we will suffer adverse tax consequences, including possible loss of favorable regulated investment company tax treatment. We cannot assure stockholders that they will receive any distributions.
If we do not distribute a certain percentage of our income annually, we will suffer adverse tax consequences, including possible loss of favorable RIC tax treatment. We cannot assure stockholders that they will receive any distributions.
Equity securities are not graded. As of December 31, 2022 and 2021 our portfolio had a weighted average grade of 2.2 and 2.1, respectively, based upon the fair value of the debt investments in the portfolio.
Equity securities are not graded. As of December 31, 2023 and 2022 our portfolio had a weighted average grade of 2.3 and 2.2, respectively, based upon the fair value of the debt investments in the portfolio.
Qualifying assets must represent at least 70% of the Company’s total assets at the time of acquisition of any additional non -qualifying assets. As of December 31, 2022 and 2021, we held qualifying assets that represented 70.1% and 64.1%, respectively, of the total assets.
Qualifying assets must represent at least 70% of the Company’s total assets at the time of acquisition of any additional non -qualifying assets. As of December 31, 2023 and 2022, we held qualifying assets that represented 70.6% and 70.1%, respectively, of the total assets.
In addition, we receive principal repayments of some of our investments prior to their scheduled maturity date. The frequency or volume of these repayments may fluctuate significantly from period to period. For the years ended December 31, 2022 and December 31, 2021, we had loan principal repayments of approximately $50.0 million and approximately $24.3 million, respectively.
In addition, we receive principal repayments of some of our investments prior to their scheduled maturity date. The frequency or volume of these repayments may fluctuate significantly from period to period. For the years ended December 31, 2023 and December 31, 2022, we had loan principal repayments of approximately $15.8 million and approximately $50.0 million, respectively.
The following table indicates the quarterly portfolio investment activity for the years ended December 31, 2022 and 2021: ($ in millions) Purchases of Investments Repayments of Principal Sales of Investments Reductions to CLO Equity Cost (1) Quarter ended December 31, 2022 $ 6.1 $ 0.2 $ — $ 2.3 September 30, 2022 3.9 11.0 1.8 3.9 June 30, 2022 26.9 0.2 9.5 6.4 March 31, 2022 47.4 38.6 3.4 7.8 Total (2) $ 84.2 $ 50.0 $ 14.6 $ 20.4 December 31, 2021 $ 23.3 $ 1.6 $ 10.3 $ 7.4 September 30, 2021 23.1 5.7 — 8.6 June 30, 2021 99.5 0.6 3.0 15.5 March 31, 2021 32.9 16.4 1.8 6.0 Total (2) $ 178.9 $ 24.3 $ 15.2 $ 37.5 ____________ (1) Represents reductions to CLO equity cost value (representing distributions received, or entitled to be received, in excess of effective yield interest income and amortized cost adjusted CLO fee note income).
The following table indicates the quarterly portfolio investment activity for the years ended December 31, 2023 and 2022: ($ in millions) Purchases of Investments Repayments of Principal Sales of Investments Reductions to CLO Equity Cost (1) Quarter ended December 31, 2023 $ 3.5 $ 0.8 $ 3.7 $ 2.8 September 30, 2023 — 14.2 1.9 5.1 June 30, 2023 — 0.4 13.9 4.4 March 31, 2023 8.2 0.3 — 3.0 Total (2) $ 11.7 $ 15.8 $ 19.6 $ 15.3 December 31, 2022 $ 6.1 $ 0.2 $ — $ 2.3 September 30, 2022 3.9 11.0 1.8 3.9 June 30, 2022 26.9 0.2 9.5 6.4 March 31, 2022 47.4 38.6 3.4 7.8 Total (2) $ 84.2 $ 50.0 $ 14.6 $ 20.4 ____________ (1) Represents reductions to CLO equity cost value (representing distributions received, or entitled to be received, in excess of effective yield interest income and amortized cost adjusted CLO fee note income).
For the year ended December 31, 2022, the net increase in net assets resulting from net investment income per common share was $0.42 (basic and diluted), compared to $0.32 (basic and diluted) for the year ended December 31, 2021, based on the weighted average common shares outstanding for the respective period.
For the year ended December 31, 2023, the net increase in net assets resulting from net investment income per common share was $0.51 (basic and diluted), compared to $0.42 (basic and diluted) for the year ended December 31, 2022, based on the weighted average common shares outstanding for the respective periods.
Oxford Square Management, Oxford Lane Management, LLC and Oxford Gate Management, LLC are subject to a written policy with respect to the allocation of investment opportunities among the Company, Oxford Lane Capital Corp., Oxford Bridge II, LLC and the Oxford Gate Funds.
Oxford Square Management, Oxford Lane Management, Oxford Park Management and Oxford Gate Management are subject to a written policy with respect to the allocation of investment opportunities among the Company, Oxford Lane Capital Corp., Oxford Park Income Fund, Inc., Oxford Bridge II, LLC and the Oxford 78 Gate Funds.
In connection with that determination, members of Oxford Square Management’s portfolio management team prepare a quarterly analysis of each portfolio investment using the most recent portfolio company financial statements, forecasts and other relevant financial and operational information.
Our Board of Directors determines the value of our investment portfolio each quarter. In connection with that determination, members of Oxford Square Management’s portfolio management team prepare a quarterly analysis of each portfolio investment using the most recent portfolio company financial statements, forecasts and other relevant financial and operational information.
When we receive a warrant to purchase stock in a portfolio company, the warrant will typically have a nominal strike price, and will entitle us to purchase a modest percentage of the borrower’s stock. 65 PORTFOLIO COMPOSITION AND INVESTMENT ACTIVITY The total fair value of our investment portfolio was approximately $314.7 million and $420.8 million as of December 31, 2022 and December 31, 2021, respectively.
When we receive a warrant to purchase stock in a portfolio company, the warrant will typically have a nominal strike price, and will entitle us to purchase a modest percentage of the borrower’s stock. 66 PORTFOLIO COMPOSITION AND INVESTMENT ACTIVITY The total fair value of our investment portfolio was approximately $266.9 million and $314.7 million as of December 31, 2023 and December 31, 2022, respectively.
At December 31, 2022 and 2021, our debt investment portfolio was graded as follows: ($ in millions) December 31, 2022 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 230.1 74.9 % 180.0 85.1 % 3 Closer monitoring is required.
At December 31, 2023 and 2022, our debt investment portfolio was graded as follows: ($ in millions) December 31, 2023 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 175.5 60.4 % 134.5 74.9 % 3 Closer monitoring is required.
In light of these and other uncertainties, the inclusion of a projection or forward -looking statement in this annual report on Form 10 -K should not be regarded as a representation by us that our plans and objectives will be achieved.
In light of these and other uncertainties, the inclusion of a projection or forward -looking statement in this annual report on Form 10 -K should not be regarded as a representation by us that our plans and objectives will be achieved. These risks and uncertainties include those described or identified in Item 1A.
The aggregate accrued interest which remained payable as of December 31, 2022 and 2021 was approximately $1.2 million. The Base Fee decreased approximately $383,000 in 2022 compared to 2021 due to lower average adjusted gross assets in 2022.
The aggregate accrued interest which remained payable as of December 31, 2023 and 2022 was approximately $1.2 million. The Base Fee decreased by approximately $1.3 million in 2023 compared to 2022 due to lower average adjusted gross assets in 2023.
In valuing such investments, we consider the indicative prices provided by a recognized industry pricing service as a primary source, and the implied yield of such prices, supplemented by actual trades executed in the market at or around period -end , as well as the indicative prices provided by the broker who arranges transactions in such investment vehicles.
In valuing our CLO debt and equity investments, we consider the indicative prices provided by a recognized industry pricing service as a primary source, and the implied yield of such prices, supplemented by actual trades executed in the market at or around period -end , as well as the indicative prices provided by brokers who arrange transactions in such investment vehicles.
These statements are not guarantees of future performance and are subject to risks, uncertainties, and other factors, some of which are beyond our control and difficult to predict and could cause actual results to differ materially from those expressed or forecasted in the forward -looking statements, including without limitation: • an economic downturn could impair our portfolio companies’ and CLO investments’ ability to continue to operate, which could lead to the loss of some or all of our investments in such portfolio companies and CLO investments; • the impact of the elimination of the London Interbank Offered Rate (“LIBOR”) and implementation of alternatives to LIBOR on our operating results; • a contraction of available credit and/or an inability to access the equity markets, including as a result of the current COVID -19 pandemic, could impair our lending and investment activities; • interest rate volatility could adversely affect our results, particularly because we use leverage as part of our investment strategy; • the elevated levels of inflation and its impact on our investment activities and the industries in which we invest; • currency fluctuations could adversely affect the results of our investments in foreign companies, particularly to the extent that we receive payments denominated in foreign currency rather than U.S. dollars; • the impact of information technology system failures, data security breaches, data privacy compliance, network disruptions and cybersecurity attacks; and • the risks, uncertainties and other factors we identify in Item 1A. — Risk Factors and elsewhere in this Annual Report on Form 10 -K and in our filings with the SEC.
These statements are not guarantees of future performance and are subject to risks, uncertainties, and other factors, some of which are beyond our control and difficult to predict and could cause actual results to differ materially from those expressed or forecasted in the forward -looking statements, including without limitation: • an economic downturn could impair our portfolio companies’ and CLO investments’ ability to continue to operate, which could lead to the loss of some or all of our investments in such portfolio companies and CLO investments; • a contraction of available credit and/or an inability to access the equity markets could impair our lending and investment activities; • interest rate volatility could adversely affect our results, particularly because we use leverage as part of our investment strategy; • the elevated levels of inflation and its impact on our investment activities and the industries in which we invest; • currency fluctuations could adversely affect the results of our investments in foreign companies, particularly to the extent that we receive payments denominated in foreign currency rather than U.S. dollars; • the impact of information technology system failures, data security breaches, data privacy compliance, network disruptions and cybersecurity attacks; and • the risks, uncertainties and other factors we identify in Item 1A.
A reconciliation of the investment portfolio for the years ended December 31, 2022 and 2021 follows: ($ in millions) December 31, 2022 December 31, 2021 Beginning investment portfolio $ 420.8 $ 294.7 Portfolio investments acquired 84.2 178.9 Debt repayments (50.0 ) (24.3 ) Sales of securities (14.6 ) (15.2 ) Reductions to CLO equity cost value (1) (20.4 ) (37.5 ) Accretion of discounts on investments (2) 0.9 0.7 Net change in unrealized (depreciation)/appreciation on investments (105.9 ) 38.5 Net realized loss on investments (0.3 ) (15.0 ) Ending investment portfolio $ 314.7 $ 420.8 ____________ (1) For the year ended December 31, 2022, the reductions to CLO equity cost value of approximately $20.4 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $37.3 million, plus the amortization of cost on our CLO fee notes of approximately $128,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $17.1 million.
A reconciliation of the investment portfolio for the years ended December 31, 2023 and 2022 follows: ($ in millions) December 31, 2023 December 31, 2022 Beginning investment portfolio $ 314.7 $ 420.8 Portfolio investments acquired 11.7 84.2 Debt repayments (15.8 ) (50.0 ) Sales of securities (19.6 ) (14.6 ) Reductions to CLO equity cost value (1) (15.3 ) (20.4 ) Accretion of discounts on investments 1.1 0.9 Net change in unrealized appreciation/(depreciation) on investments 7.1 (105.9 ) Net realized losses on investments (17.1 ) (0.3 ) Ending investment portfolio (2) $ 266.9 $ 314.7 ____________ (1) For the year ended December 31, 2023, the reductions to CLO equity cost value of approximately $15.3 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $32.0 million, plus the amortization of cost on our CLO fee notes of approximately $123,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $16.8 million.
A summary of our significant contractual payment obligations is as follows as of December 31, 2022. Refer to “Note 5. Borrowings” in the notes to our financial statements.
Related Party Transactions” in the notes to our financial statements. A summary of our significant contractual payment obligations is as follows as of December 31, 2023. Refer to “Note 5. Borrowings” in the notes to our financial statements.
RECENT DEVELOPMENTS The following distributions payable to stockholders are shown below: Date Declared Record Dates Payable Dates Per Share Distribution Amount Declared October 20, 2022 January 17, 2023 January 31, 2023 $ 0.035 October 20, 2022 February 14, 2023 February 28, 2023 $ 0.035 October 20, 2022 March 17, 2023 March 31, 2023 $ 0.035 March 16, 2023 April 14, 2023 April 28, 2023 $ 0.035 March 16, 2023 May 17, 2023 May 31, 2023 $ 0.035 March 16, 2023 June 16, 2023 June 30, 2023 $ 0.035
RECENT DEVELOPMENTS The following distributions payable to stockholders are shown below: Date Declared Record Dates Payable Dates Per Share Distribution Amount Declared November 2, 2023 January 17, 2024 January 31, 2024 $ 0.035 November 2, 2023 February 15, 2024 February 29, 2024 $ 0.035 November 2, 2023 March 15, 2024 March 29, 2024 $ 0.035 March 14, 2024 April 16, 2024 April 30, 2024 $ 0.035 March 14, 2024 May 17, 2024 May 31, 2024 $ 0.035 March 14, 2024 June 14, 2024 June 28, 2024 $ 0.035
This includes net unrealized appreciation of approximately $37.5 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $55.8 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $18.3 million.
This includes net unrealized appreciation of approximately $15.3 million resulting from reductions to the cost value of our CLO equity investments representing the difference between distributions received, or entitled to be received, on our investments held in CLO equity subordinated notes and fee notes, of approximately $32.0 million and the effective yield interest income recognized on our CLO equity subordinated notes and the amortized cost adjusted income on our CLO equity fee notes of approximately $16.7 million.
The following table shows the fair value of our portfolio of investments by asset class as of December 31, 2022 and 2021: December 31, 2022 December 31, 2021 ($ in millions) Investments at Fair Value Percentage of Total Portfolio Investments at Fair Value Percentage of Total Portfolio Senior Secured Notes $ 211.4 67.2 % $ 264.5 62.8 % CLO Equity 98.9 31.4 % 155.6 37.0 % Equity and Other Investments 4.3 1.4 % 0.8 0.2 % Total (1) $ 314.7 100.0 % $ 420.8 100.0 % ____________ (1) Totals may not sum due to rounding.
The following table shows the fair value of our portfolio of investments by asset class as of December 31, 2023 and 2022: December 31, 2023 December 31, 2022 ($ in millions) Investments at Fair Value Percentage of Total Portfolio Investments at Fair Value Percentage of Total Portfolio Senior Secured Notes $ 179.5 67.2 % $ 211.4 67.2 % CLO Equity 82.2 30.8 % 98.9 31.4 % Equity and Other Investments 5.3 2.0 % 4.3 1.4 % Total (1) $ 266.9 100.0 % $ 314.7 100.0 % ____________ (1) Totals may not sum due to rounding.
Compensation expense was approximately $916,000 for the year ended December 31, 2022, compared to approximately $724,000 for the year ended December 31, 2021, reflecting the allocation of compensation expenses for the services of our Chief Financial Officer, accounting personnel, and other administrative support staff. As of December 31, 2022, approximately $31,000 in compensation expenses remained payable.
Compensation expense was approximately $825,000 for the year ended December 31, 2023, compared to approximately $916,000 for the year ended December 31, 2022, reflecting the allocation of compensation expenses for the services of our Chief Financial Officer, accounting personnel, and other administrative support staff. As of December 31, 2023, there was no compensation expense payable.
In addition, our total portfolio had a weighted average annualized yield on debt investments of approximately 11.85%.
In addition, our total portfolio had a weighted average annualized yield on debt investments of approximately 13.30%.
As of December 31, 2022, our debt investments had stated interest rates of between 7.63% and 14.24% and maturity dates of between 1 and 86 months. As of December 31, 2021, our debt investments had stated interest rates of between 3.85% and 10.50% and maturity dates of between 3 and 91 months.
As of December 31, 2022, our debt investments had stated interest rates of between 7.63% and 14.24% and maturity dates of between 1 and 86 months.
Rubin serves as the Chief Financial Officer and Secretary, and Gerald Cummins serves as the Chief Compliance Officer, respectively, of Oxford Gate Management, LLC. • Messrs.
In addition, Bruce L. Rubin serves as the Chief Financial Officer and Secretary, and Gerald Cummins serves as the Chief Compliance Officer, respectively, of Oxford Gate Management. • Messrs.
Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 14.7 4.9 % 13.9 5.3 % 4 A loss of interest income has occurred or is expected to occur and, in most cases, the investment is placed on non-accrual status.
Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 72.3 24.8 % 43.3 24.1 % 4 A loss of interest income has occurred or is expected to occur and, in most cases, the investment is placed on non-accrual status.
No additional non -qualifying assets were acquired during the periods, if any, when qualifying assets were less than 70% of the total assets. 67 The following table shows our portfolio of investments by industry at fair value, in millions, as of December 31, 2022 and 2021: December 31, 2022 December 31, 2021 Investments at Fair Value Percentage of Fair Value Investments at Fair Value Percentage of Fair Value ($ in millions) ($ in millions) Structured finance (1) $ 98.9 31.4 % $ 155.6 36.9 % Software 69.0 21.9 % 50.9 12.1 % Business services 53.4 17.0 % 88.7 21.0 % Healthcare 33.6 10.7 % 63.0 15.0 % Telecommunication services 22.2 7.1 % 15.8 3.8 % Diversified insurance 14.7 4.7 % 25.9 6.2 % Plastics Manufacturing 11.7 3.7 % 12.7 3.0 % Utilities 6.8 2.2 % 7.5 1.8 % IT consulting 4.3 1.4 % 0.8 0.2 % Total (2) $ 314.7 100.0 % $ 420.8 100.0 % ____________ (1) Reflects our equity investments in CLOs as of December 31, 2022 and December 31, 2021, respectively.
No additional non -qualifying assets were acquired during the periods, if any, when qualifying assets were less than 70% of the total assets. 68 The following table shows our portfolio of investments by industry at fair value, in millions, as of December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Investments at Fair Value Percentage of Fair Value Investments at Fair Value Percentage of Fair Value ($ in millions) ($ in millions) Structured finance (1) $ 82.2 30.8 % $ 98.9 31.4 % Software 66.0 24.7 % 69.0 21.9 % Business services 43.0 16.1 % 53.4 17.0 % Healthcare 28.4 10.7 % 33.6 10.7 % Telecommunication services 20.9 7.8 % 22.2 7.0 % Diversified insurance 13.9 5.2 % 14.7 4.7 % Utilities 7.2 2.7 % 6.8 2.2 % IT consulting 5.3 2.0 % 4.3 1.4 % Plastics manufacturing — — % 11.7 3.7 % Total (2) $ 266.9 100.0 % $ 314.7 100.0 % ____________ (1) Reflects our equity investments in CLOs as of December 31, 2023 and December 31, 2022, respectively.
As of December 31, 2021, no compensation expenses remained payable. General and administrative expenses, which consist primarily of listing fees, office supplies, facilities costs and other miscellaneous expenses, increased by approximately $314,000 in 2022 compared to 2021.
As of December 31, 2022, approximately $31,000 in compensation expenses remained payable. General and administrative expenses, which consist primarily of listing fees, office supplies, facilities costs and other miscellaneous expenses, increased by approximately $55,000 for the year ended December 31, 2023 compared to the year ended December 31, 2022.
These risks and uncertainties include those described or identified in Item 1A. — Risk Factors and elsewhere in this annual report on Form 10 -K . You should not place undue reliance on these forward -looking statements, which apply only as of the date of this annual report on Form 10 -K .
Risk Factors and elsewhere in this annual report on Form 10 -K . You should not place undue reliance on these forward -looking statements, which apply only as of the date of this annual report on Form 10 -K .
The tables below summarize the components of interest expense for the years ended December 31, 2022 and 2021: Year Ended December 31, 2022 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Total 6.50% Unsecured Notes $ 4,184.1 $ 324.7 $ 4,508.8 6.25% Unsecured Notes 2,799.4 233.2 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 4,813.0 Total $ 11,411.0 $ 943.4 $ 12,354.4 Year Ended December 31, 2021 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Total 6.50% Unsecured Notes $ 4,184.1 $ 324.7 $ 4,508.8 6.25% Unsecured Notes 2,799.4 233.2 3,032.6 5.50% Unsecured Notes 2,718.0 236.6 2,954.5 Total (1) $ 9,701.5 $ 794.4 $ 10,495.9 ____________ (1) Totals may not sum due to rounding.
The tables below summarize the components of interest expense for the years ended December 31, 2023 and 2022: Year Ended December 31, 2023 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Loss on Extinguishment Total 6.50% Unsecured Notes $ 2,765.0 $ 215.3 $ 190.4 $ 3,170.6 6.25% Unsecured Notes 2,799.4 233.2 — 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 — 4,813.0 Total $ 9,991.9 $ 834.0 $ 190.4 $ 11,016.2 Year Ended December 31, 2022 ($ in thousands) Stated Interest Expense Amortization of Deferred Debt Issuance Costs Total 6.50% Unsecured Notes $ 4,184.1 $ 324.7 $ 4,508.8 6.25% Unsecured Notes 2,799.4 233.2 3,032.6 5.50% Unsecured Notes 4,427.5 385.5 4,813.0 Total $ 11,411.0 $ 943.4 $ 12,354.4 ____________ (1) Totals may not sum due to rounding.
For the year ended December 31, 2021, the reductions to CLO equity cost value of approximately $37.5 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $55.8 million, plus the amortization of cost on our CLO fee notes of approximately $351,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $18.7 million.
For the year ended December 31, 2022, the reductions to CLO equity cost value of approximately $20.4 million represented the distributions received, or entitled to be received, on our investments held in CLO equity subordinated and income notes of approximately $37.3 million, plus the amortization of cost on our CLO fee notes of approximately $128,000, less the effective yield interest income recognized on our CLO equity subordinated and income notes of approximately $17.1 million.
We expect that our investment portfolio will be diversified among a large number of investments with few investments, if any, exceeding 5.0% of the total portfolio. As of December 31, 2022, our debt investments had stated interest rates of between 7.63% and 14.24% and maturity dates of between 1 and 86 months.
We expect that our investment portfolio will be diversified among a large number of investments with few investments, if any, exceeding 5.0% of the total portfolio. As of December 31, 2023, our debt investments had stated interest rates of between 9.22% and 16.00% and maturity dates of between 0 and 74 months.
During the year ended December 31, 2022, we purchased approximately $84.2 million in portfolio investments, including additional investments of approximately $58.9 million in existing portfolio companies and approximately $25.3 million in new portfolio companies.
During the year ended December 31, 2022, we purchased approximately $84.2 million in portfolio investments, including additional investments of approximately $58.9 million in existing portfolio companies and approximately $25.3 million in new portfolio companies. In certain instances, we receive payments based on scheduled amortization of the outstanding balances.
(14.6 ) Net all other 13.9 Total (1) $ 38.5 ____________ (1) Totals may not sum due to rounding. Net Increase in Net Assets Resulting from Net Investment Income Net investment income for the year ended December 31, 2022 was approximately $20.7 million, compared to $16.1 million for the year ended December 31, 2021.
(3.7 ) Net all other (43.4 ) Total (1) $ (105.9 ) ____________ (1) Totals may not sum due to rounding. Net Increase in Net Assets Resulting from Net Investment Income Net investment income for the year ended December 31, 2023 was approximately $27.4 million, compared to $20.7 million for the year ended December 31, 2022.
Realized and Unrealized Gains/Losses on Investments For the year ended December 31, 2022, we recognized net realized losses on investments of approximately $340,000, which primarily represents offsetting gains and losses from sales and repayments of multiple CLO equity investments.
Realized and Unrealized Gains/Losses on Investments For the year ended December 31, 2023, we recognized net realized losses on investments of approximately $17.1 million, which primarily represents sales of multiple CLO equity investments.
The decrease in the value of investments during the year ended December 31, 2022 was due primarily to a net change in unrealized depreciation on our investment portfolio of approximately $105.9 million (which incorporates reductions to CLO equity cost value of $20.4 million), repayments of principal and sales of securities totaling approximately $64.6 million, partially offset by purchases of investments of approximately $84.2 million.
The decrease in the value of investments during the year ended December 31, 2023 was due primarily to repayments of principal of approximately $15.8 million and sales of securities totaling approximately $19.6 million, partially offset by a net change in unrealized appreciation on our investment portfolio of approximately $7.1 million (which incorporates reductions to CLO equity cost value of $15.3 million) and purchases of investments of approximately $11.7 million.
Cohen and Rosenthal also currently serve as Chief Executive Officer and President, respectively, at Oxford Gate Management, LLC, the investment adviser to the Oxford Gate Funds and Oxford Bridge II, LLC. Oxford Funds is the managing member of Oxford Gate Management, LLC. In addition, Bruce L.
In addition, Oxford Funds provides us with office facilities and administrative services pursuant to the Administration Agreement. • Messrs. Cohen and Rosenthal also currently serve as Chief Executive Officer and President, respectively, at Oxford Gate Management, the investment adviser to the Oxford Gate Funds and Oxford Bridge II, LLC. Oxford Funds is the managing member of Oxford Gate Management.
As of ($ in millions) December 31, 2022 December 31, 2021 Principal Amount Carrying Value Fair Value Principal Amount Carrying Value Fair Value 6.50% Unsecured Notes $ 64.4 $ 64.0 $ 63.4 $ 64.4 $ 63.6 $ 65.1 6.25% Unsecured Notes 44.8 44.0 42.6 44.8 43.8 45.5 5.50% Unsecured Notes 80.5 78.3 70.0 80.5 78.0 80.7 Total $ 189.7 $ 186.3 $ 176.0 $ 189.7 $ 185.4 $ 191.3 74 The weighted average stated interest rate and weighted average maturity on all our debt outstanding as of December 31, 2022 were 6.02% and 3.6 years, respectively, and as of December 31, 2021 were 6.02% and 4.6 years, respectively.
As of ($ in millions) December 31, 2023 December 31, 2022 Principal Amount Carrying Value Fair Value Principal Amount Carrying Value Fair Value 6.50% Unsecured Notes $ — $ — $ — $ 64.4 $ 64.0 $ 63.4 6.25% Unsecured Notes 44.8 44.2 42.9 44.8 44.0 42.6 5.50% Unsecured Notes 80.5 78.7 72.5 80.5 78.3 70.0 Total (1) $ 125.3 $ 123.0 $ 115.4 $ 189.7 $ 186.3 $ 176.0 ____________ (1) Totals may not sum due to rounding. 75 The weighted average stated interest rate and weighted average maturity on all our debt outstanding as of December 31, 2023 were 5.77% and 3.8 years, respectively, and as of December 31, 2022 were 6.02% and 3.6 years, respectively.
Although we believe that the assumptions on which these forward -looking statements are based are reasonable, any of those assumptions could prove to be inaccurate, and as a result, the forward -looking statements based on those assumptions also could be inaccurate.
Risk Factors and elsewhere in this Annual Report on Form 10 -K and in our filings with the SEC. Although we believe that the assumptions on which these forward -looking statements are based are reasonable, any of those assumptions could prove to be inaccurate, and as a result, the forward -looking statements based on those assumptions also could be inaccurate.
For the year ended December 31, 2021, our net change in unrealized appreciation was approximately $38.5 million, composed of approximately $40.0 million in gross unrealized appreciation, approximately $20.4 million in gross unrealized depreciation and approximately $18.9 million relating to the reversal of prior 72 period net unrealized depreciation as investment gains and losses were realized.
For the year ended December 31, 2023, our net change in unrealized appreciation was approximately $7.1 million, composed of approximately $16.6 million in gross unrealized appreciation, approximately $28.7 million in gross unrealized depreciation and approximately $19.2 million relating to the reversal of prior period net unrealized depreciation as investment gains and losses were realized.
($ in millions) December 31, 2021 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 256.3 86.1 % 249.2 94.2 % 3 Closer monitoring is required.
Full repayment of the outstanding amount of OXSQ’s cost basis is expected for the specific tranche. — — % — — % 5 Full repayment of the outstanding amount of OXSQ’s cost basis is not expected for the specific tranche and the investment is placed on non-accrual status 42.9 14.8 % 1.7 1.0 % Total $ 290.7 100.0 % $ 179.5 100.0 % ($ in millions) December 31, 2022 Grade Summary Description Principal Value Percentage of Debt Portfolio Portfolio at Fair Value Percentage of Debt Portfolio 1 Company is ahead of expectations and/or outperforming financial covenant requirements of the specific tranche and such trend is expected to continue. $ — — % $ — — % 2 Full repayment of the outstanding amount of OXSQ’s cost basis and interest is expected for the specific tranche. 230.1 74.9 % 180.0 85.1 % 3 Closer monitoring is required.
We did not sell any shares of common stock under the ATM program during the years ended December 31, 2022 and 2021. Borrowings In accordance with the 1940 Act, with certain limited exceptions, we are only allowed to borrow amounts such that our asset coverage, as defined in the 1940 Act, is at least 150% immediately after such borrowing.
Borrowings In accordance with the 1940 Act, with certain limited exceptions, we are only allowed to borrow amounts such that our asset coverage, as defined in the 1940 Act, is at least 150% immediately after such borrowing. As of December 31, 2023, our asset coverage for borrowed amounts was approximately 219%.
Net cash used in operating activities for the year ended December 31, 2022, consisting primarily of the items described in “— Results of Operations,” was approximately $20.4 million, largely reflecting purchases of new investments of approximately $84.2 million, partially offset by repayments of principal of approximately $50.0 million and proceeds from the sale of investments of approximately $14.6 million.
Net cash provided by operating activities for the year ended December 31, 2023, consisting primarily of the items described in “— Results of Operations,” was approximately $65.7 million, largely reflecting repayments of principal of approximately $15.8 million, proceeds from the sale of investments of approximately $19.6 million and reductions to CLO equity cost value of approximately $15.3 million, partially offset by purchases of new investments of approximately $11.7 million.
The calculation of the Net Investment Income Incentive Fee had no change in 2022 compared to 2021. There was no Net Investment Income Incentive Fee in 2022, nor in 2021, primarily as a result of the Net Investment Income Incentive Fee being reduced as the result of the Total Return Requirement.
There was no Net Investment Income Incentive Fee for the year ended December 31, 2022, primarily as a result of the Net Investment Income Incentive Fee being reduced as the result of the Total Return Requirement.
LIQUIDITY AND CAPITAL RESOURCES During the year ended December 31, 2022, cash and cash equivalents increased from $9,015,700 at the beginning of the period to $9,019,164 at the end of the period.
LIQUIDITY AND CAPITAL RESOURCES During the year ended December 31, 2023, cash and cash equivalents decreased from approximately $9.0 million at the beginning of the period to approximately $5.7 million at the end of the period.
Investment Income The following table sets forth the components of investment income for the years ended December 31, 2022 and 2021: December 31, 2022 December 31, 2021 Interest Income Stated interest income $ 23,954,078 $ 16,142,294 Original issue discount and market discount income 880,671 740,731 Discount income derived from unscheduled remittances at par 399,566 557,204 Total interest income 25,234,315 17,440,229 Income from securitization vehicles and investments 17,093,203 18,691,631 Other income Fee letters 544,267 405,010 Loan prepayment and bond call fees — 300,000 All other fees 246,327 338,143 Total other income 790,594 1,043,153 Total investment income $ 43,118,112 $ 37,175,013 The increase in total investment income for the year ended December 31, 2022 compared to the year ended December 31, 2021 was largely due to an increase of stated interest income from our debt investments (approximately $7.8 million) resulting from higher weighted average yields in 2022 compared to 2021.
Investment Income The following table sets forth the components of investment income for the years ended December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Interest Income Stated interest income $ 32,434,732 $ 23,954,078 Original issue discount and market discount income 1,094,874 880,671 Discount income derived from unscheduled remittances at par 62,560 399,566 Total interest income 33,592,166 25,234,315 Income from securitization vehicles and investments 16,796,699 17,093,203 Other income Fee letters 649,260 544,267 Money market fund income and all other fees 786,056 246,327 Total other income 1,435,316 790,594 Total investment income $ 51,824,181 $ 43,118,112 The increase in total investment income of approximately $8.7 million for the year ended December 31, 2023 over the year ended December 31, 2022 was largely due to an increase of stated interest income from our debt investments (approximately $8.5 million) resulting from higher weighted average yields in 2023 compared to 2022.
Net Decrease/Increase in Net Assets Resulting from Operations Net decrease in net assets resulting from operations for the year ended December 31, 2022 was approximately $85.6 million, compared to a net increase of $39.6 million for year ended December 31, 2021. These changes were largely due to a net change in unrealized depreciation, as discussed above.
Net Increase/Decrease in Net Assets Resulting from Operations Net increase in net assets resulting from operations for the year ended December 31, 2023 was approximately $17.2 million, compared to a net decrease of $85.6 million for year ended December 31, 2022.
Oxford Square Management is controlled by Oxford Funds, its managing member. In addition to Oxford Funds, Oxford Square Management is owned by Charles M. Royce, a member of our Board, who holds a minority, non -controlling interest in Oxford Square Management as the non -managing member.
Royce, a member of our Board, who holds a minority, non -controlling interest in Oxford Square Management as the non -managing member. Oxford Funds, as the managing member of Oxford Square Management, manages the business and internal affairs of Oxford Square Management.
In addition, our total portfolio had a weighted average yield on debt investments of approximately 11.85% as of December 31, 2022, compared to a weighted average yield on debt investments of 7.70% as of December 31, 2021. 70 Operating Expenses The following table sets forth the components of operating expenses for the years ended December 31, 2022 and 2021: December 31, 2022 December 31, 2021 Interest expense $ 12,354,392 $ 10,495,897 Base Fee 5,903,986 6,287,173 Professional fees 1,393,116 1,910,390 Compensation expense 915,583 723,931 General and administrative 835,912 521,541 Director’s fees 417,500 490,500 Insurance 378,804 422,805 Transfer agent and custodian fees 231,241 222,581 Net Investment Income Incentive Fees — — Total operating expenses $ 22,430,534 $ 21,074,818 Total operating expenses for the year ended December 31, 2022 increased by approximately $1.4 million compared to the year ended December 31, 2021.
In addition, our total portfolio had a weighted average yield on debt investments of approximately 13.30% as of December 31, 2023, compared to a weighted average yield on debt investments of 11.85% as of December 31, 2022. 71 Operating Expenses The following table sets forth the components of operating expenses for the years ended December 31, 2023 and 2022: December 31, 2023 December 31, 2022 Interest expense $ 10,825,877 $ 12,354,392 Base Fee 4,613,664 5,903,986 Net Investment Income Incentive Fees 3,705,387 — Professional fees 1,426,098 1,393,116 Excise Tax 1,423,686 252,172 Compensation expense 825,226 915,583 General and administrative 638,350 583,740 Director’s fees 429,500 417,500 Insurance 329,892 378,804 Transfer agent and custodian fees 246,562 231,241 Total operating expenses $ 24,464,242 $ 22,430,534 Total operating expenses for the year ended December 31, 2023 increased by approximately $2.0 million compared to the year ended December 31, 2022.
Oxford Funds, as the managing member of Oxford Square Management, manages the business and internal affairs of Oxford Square Management. In addition, Oxford Funds provides us with office facilities and administrative services pursuant to the Administration Agreement. • Messrs.
Oxford Funds provides Oxford Park Income Fund, Inc. with office facilities and administrative services pursuant to an administration agreement and also serves as the managing member of Oxford Park Management. In addition, Bruce L.
Oxford Square Management or the Valuation Committee may request an additional analysis by a third -party firm to assist in the valuation process of CLO investment vehicles.
Oxford Square Management or the Valuation Committee may request an additional analysis by a third -party firm to assist in the valuation process of CLO investment vehicles. All information is presented to our Board for its determination of fair value of these investments. Recently Issued Accounting Standards See “Note 16.
The Base Fee which remained payable to Oxford Square Management as of December 31, 2022 and 2021 was approximately $1.3 million and $1.7 million, respectively. Professional fees, largely consisting of legal, valuation, consulting, audit and tax fees decreased by approximately $517,000 in 2022 compared to 2021 primarily due to decreased legal fees.
The Base Fee which remained payable to Oxford Square Management as of December 31, 2023 and 2022 was approximately $1.0 million and $1.3 million, respectively.