Investor Update – November 2022

Investor Disclosures

Forward Looking Statements

This presentation contains "forward-looking statements" which are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. The forward-looking statements are based on Maiden Holdings, Ltd.'s (the "Company") future developments and their potential effects on the Company. There can be no assurance that actual developments will be those anticipated by the Company. Actual results may differ materially from those projected as a result of significant risks and uncertainties, including non-receipt of the expected payments, changes in interest rates, effect of the performance of financial markets on investment income and fair values of investments, developments of claims and the effect on loss reserves, accuracy in projecting loss reserves, the impact of competition and pricing environments, changes in the demand for the Company's products, the effect of general economic conditions and unusual frequency of storm activity, adverse state and federal legislation, regulations and regulatory investigations into industry practices, developments relating to existing agreements, heightened competition, changes in pricing environments, and changes in asset valuations. Additional information about these risks and uncertainties, as well as others that may cause actual results to differ materially from those projected is contained in Item 1A. Risk Factors in the Company's Annual Report on Form 10-K for the year ended December 31, 2021, filed with the SEC. The Company undertakes no obligation to publicly update any forward-looking statements, except as may be required by law. Any discrepancies between the amounts included in this presentation and amounts included in the Company's Form 10-Q for the three and nine months ended September 30, 2022, filed with the SEC are due to rounding.

Non-GAAP Financial Measures

In addition to the Summary Consolidated Balance Sheets and Consolidated Statements of Income, management uses certain key financial measures, some of which are non-GAAP measures, to evaluate the Company's financial performance and the overall growth in value generated for the Company's common shareholders. Management believes that these measures, which may be defined differently by other companies, explain the Company's results to investors in a manner that allows for a more complete understanding of the underlying trends in the Company's business. The non-GAAP measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. See the Appendix of this presentation for a reconciliation of the Company's non-GAAP measures to the nearest GAAP measure.

1

Maiden Holdings Q3 2022 Highlights

• On November 9, Maiden announced plans to exchange all preference shares for its common shares

1. Exchange offers preference shareholders enhanced liquidity and value while accretive to Maiden shareholders and simplifying Maiden's balance sheet - see slide 9 for further information
2. • Estimate the exchange will significantly increase book value by approximately $0.82 per common share while creating value and liquidity for preference shareholders

• 1. Capital management - repurchased $176.4m preference shares since Q4 2020, increasing book value by $1.81 per common share through 9/30/2022 - no repurchases made in Q3
  2. • Maiden Reinsurance owns more than 73% of each series of preference shares and has consented to the exchange
• Q3 GAAP book value decreased to $2.38 per common share
• 1. Adjusted book value decreased to $2.79 per common share

1. Unrealized bond losses resulting from rising interest rates as well as net loss due to weaker underwriting results were the principal drivers of book value change in Q3

• 1. Book value benefitted from net long position in non-USD liabilities as US dollar continued to strengthen
• GAAP net loss available to common shareholders was $8.2m or $0.09 per share - see recap on slide 3
• 1. Unfavorable underwriting results in AmTrust Reinsurance segment included $3.7m charge during Q3 to commute $27.6m in French Hospital Liability reserves

• 1. Investment results were lower in Q3 2022 due to continuing run-off of restricted fixed income assets and higher realized and unrealized losses in hedge fund and private credit asset classes
• Capital management complemented by continuing progress in other pillars of business strategy
• 1. Asset management - increased alternative investments by 16.9% to $263.6m in 2022 and despite difficult market environment, target investment returns are starting to emerge

• 1. Legacy underwriting - near-term growth prospects for Genesis Legacy Solutions ("GLS") are strong with nearly $30m in insurance liabilities at 9/30/2022
• Deferred tax asset = $1.39 per share at September 30, 2022 - still carries full valuation allowance
• 1. Not recognized as an asset on balance sheet currently

1. Growing (but not yet sufficient) positive evidence to reduce valuation allowance2

* Please see the definition of non-GAAP financial measures in the Appendix of this presentation for additional important information regarding certain terms used herein

Maiden Holdings - Q3 2022 Results Recap

Maiden Holdings - YTD Q3 2022 Results Recap

Net Income and Per Share Data

Key Income Statement Details