Form 8-K

8-K — OPPENHEIMER HOLDINGS INC

Accession: 0001628280-26-030194

Filed: 2026-05-05

Period: 2026-05-04

CIK: 0000791963

SIC: 6211 (SECURITY BROKERS, DEALERS & FLOTATION COMPANIES)

Item: Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year

Item: Submission of Matters to a Vote of Security Holders

Item: Financial Statements and Exhibits

Documents

8-K — opy-20260504.htm (Primary)

EX-3.1 (amendedandrestatedcertif.htm)

EX-99.1 (opy2026shareholdermeetin.htm)

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8-K

8-K (Primary)

Filename: opy-20260504.htm · Sequence: 1

opy-20260504

0000791963false12/3100007919632026-05-042026-05-04

As filed with the Securities and Exchange Commission on May 5, 2026

___________________________________________________

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934

Date of report (Date of earliest event reported): May 4, 2026

OPPENHEIMER HOLDINGS INC.

(Exact name of registrant as specified in its charter)

Commission File Number 1-12043

Delaware 98-0080034

(State or other jurisdiction of (I.R.S. Employer

incorporation or organization) Identification No.)

85 Broad Street

New York, New York 10004

(Address of principal executive offices) (Zip Code)

(212) 668-8000

(Registrant's telephone number, including area code)

(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2.):

☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CRF 240.14a-12)

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class Trading Symbol Name of each exchange on which registered

Class A non-voting common Stock OPY The New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

SECTION 5 – CORPORATE GOVERNANCE AND MANAGEMENT

ITEM 5.07. Submission of Matters to a Vote of Security Holders.

The Company held the 2026 Annual Meeting of Stockholders ("2026 AM") on May 4, 2026. As of the close of business on March 6, 2026, the record date for the 2026 AM, there were 99,665 shares of Class B voting common stock, par value $0.001 per share, of the Company (the “Class B Shares”) outstanding and entitled to vote at the 2026 AM. Each Class B Share was entitled to one vote. Stockholders holding an aggregate of 97,387 Class B Shares entitled to vote at the 2026 AM, representing 97.7% of the outstanding Class B Shares as of the record date, and which constituted a quorum thereof, were present in person or represented by proxy at the 2026 AM.

At the 2026 AM, the Company’s Class B stockholders considered five voting proposals, each of which is described in more detail in the Company’s 2026 Proxy Statement.

The final voting results of each voting proposal brought before a vote of the Company’s Class B stockholders at the 2026 AM are set forth below:

Matter No. 1 - Election of Nine Directors

The nine director nominees proposed by the Board were elected to serve as members of the Board until the next annual meeting of stockholders and until their respective successors are duly elected and qualified by the following final voting results:

Name For Withheld Broker Non-Votes

Evan Behrens 97,385 2 0

Timothy M. Dwyer 97,385 2 0

Paul M. Friedman 97,385 2 0

Teresa A. Glasser 97,385 2 0

Stacy J. Kanter 97,385 2 0

Albert J. Lowenthal 97,385 2 0

Robert S. Lowenthal 97,385 2 0

R. Lawrence Roth 97,385 2 0

Suzanne E. Spaulding 97,385 2 0

Matter No. 2 - Appointment of Deloitte & Touche LLP as auditors and Authorization to Fix Remuneration

The voting proposal to ratify the appointment of Deloitte & Touche LLP as auditors of the Company for 2026 and authorize the Audit Committee to fix the auditor’s remuneration was approved by the following final voting results:

Votes For Votes Against Abstentions Broker Non-Votes

97,387 0 0 N/A

Matter No. 3 - Approval, in an advisory (non-binding) vote, of the Company’s executive compensation as disclosed in the Company’s 2026 Proxy Statement

The voting proposal to approve, in an advisory (non-binding) vote, the Company's executive compensation as disclosed in the Company's 2026 Proxy Statement was approved by the following final voting results:

Votes For Votes Against Abstentions Broker Non-Votes

97,381 2 4 0

Matter No. 4 - Approval, in an advisory (non-binding) vote, that a stockholder’s vote to approve the Company’s executive compensation (Matter 3 above) should occur every 1, 2 or 3 years

The voting proposal to approve, in an advisory (non-binding) vote, that a stockholder’s vote to approve the Company’s executive compensation (Matter 3 above) should occur every 1, 2 or 3 years was approved by the following final voting results:

Frequency of compensation 1 year 2 years 3 years Abstentions Broker Non-Votes

2 0 97,381 4 0

Matter No. 5 - Approval of the Company’s Amended and Restated Certificate of Incorporation

The voting proposal to approve the Company’s Amended and Restated Certificate of Incorporation was approved by the following final voting results:

Votes For Votes Against Abstentions Broker Non-Votes

97,381 0 6 0

SECTION 9 – FINANCIAL STATEMENTS AND EXHIBITS

ITEM 9.01. Financial Statements and Exhibits.

Exhibits:

The following Exhibit is submitted herewith.

99.1 Annual Stockholders’ Meeting Presentation dated May 4, 2026

3.1 Amended and Restated Certificate of Incorporation

10.4 The Cover Page from this Current Report on Form 8-K, Formatted in Inline XBRL

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned, hereunto duly authorized.

Oppenheimer Holdings Inc.

Date: May 5, 2026

By: /s/ Brad M. Watkins

---------------------------------

Brad M. Watkins

Chief Financial Officer

(Duly Authorized Officer)

EXHIBIT INDEX

Exhibit Number Description

99.1

Annual Stockholders’ Meeting Presentation dated May 4, 2026

3.1

Amended and Restated Certificate of Incorporation

104 The Cover Page from this Current Report on Form 8-K, Formatted in Inline XBRL

EX-3.1

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amendedandrestatedcertif

AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF OPPENHEIMER HOLDINGS INC. The undersigned Chief Executive Officer and President of Oppenheimer Holdings Inc., a corporation organized under the General Corporation Law of the State of Delaware (the “DGCL”), does execute this Amended and Restated Certificate of Incorporation and does hereby certify as follows: Article I The name of the Corporation is Oppenheimer Holdings Inc. (the “Corporation”). Article II The address of the Corporation’s registered office in the State of Delaware is 251 Little Falls Drive in the City of Wilmington, County of New Castle County. The registered agent in charge thereof is Corporation Service Company. Article III The nature of the business and purposes to be conducted or promoted by the Corporation is to engage in any lawful act or activity for which corporations may be organized under the DGCL. Article IV The total number of shares of all classes of stock which the Corporation shall have authority to issue is 100,099,665 shares, consisting solely of: 50,000,000 shares of Preferred Stock, par value $0.001 per share (the “Preferred Stock”); 50,000,000 shares of Class A Non-Voting Common Stock, par value $0.001 per share (the “Class A Common Stock”); and 99,665 shares of Class B Voting Common Stock, par value $0.001 per share (the “Class B Common Stock” and together with the Class A Common Stock, the “Common Stock”). The following is a statement of the powers, designations, preferences, relative rights, qualifications, limitations, and restrictions in respect of each class of capital stock of the Corporation. A. COMMON STOCK. 1. General. The voting, dividend and liquidation rights of the holders of Common Stock are subject to and qualified by the rights of the holders of Preferred Stock.

2. Voting. The holders of Class B Common Stock are entitled to one vote for each share held as of the record date for each meeting of stockholders. Except as expressly provided herein or as required by law, the holders of Class A Common Stock will have the same powers, rights, and preferences as, and will rank equally and share proportionately with, and be identical in all respects as to all matters to, the Class B Common Stock, including the right to attend stockholders meetings and receive informational distributions from the Corporation with respect to such meetings; provided, however, that the holders of Class A Common Stock will have no voting rights other than those voting rights required by law. There shall be no cumulative voting. 3. Dividends. Dividends may be declared and paid on the Common Stock from funds lawfully available therefor if, as and when determined by the board of directors of the Corporation (the “Board of Directors”) and subject to any preferential dividend rights of any then outstanding shares of Preferred Stock. B. PREFERRED STOCK. Preferred Stock may be issued from time to time in one or more series. The Board is authorized to fix the number of shares of any series of Preferred Stock and to determine the designation of any such series. The Board is also authorized to determine or alter the powers, rights, preferences, qualifications, restrictions, and limitations granted to or imposed upon any wholly unissued series of Preferred Stock and, within the limits and restrictions stated in any resolution or resolutions of the Board originally fixing the number of shares constituting any series, to increase or decrease (but not below the number of shares of such series then outstanding) the number of shares of any such series subsequent to the issue of shares of that series. C. GENERAL. The number of authorized shares of any class or classes of stock may be increased or decreased (but not below the number of shares thereof then outstanding) by the affirmative vote of the holders of a majority of the outstanding stock of the Corporation entitled to vote. Article V No director of the Corporation shall be personally liable to the Corporation or to any of its stockholders for monetary damages for breach of fiduciary duty as a director, notwithstanding any provision of law imposing such liability; provided, however, that to the extent required from time to time by applicable law, this Article VI shall not eliminate or limit the liability of a director, to the extent such liability is provided by applicable law, (i) for any breach of the director’s duty of loyalty to the corporation or its stockholders, (ii) for acts or omissions not in good faith or which involve intentional misconduct or a knowing violation of law, (iii) under Section 174 of the DGCL, or (iv) for any transactions from which the director derived an improper personal benefit. If the DGCL hereafter is amended to authorize the further elimination or limitation of the liability of directors, then the liability of a director of the Corporation, in addition to the limitation on personal liability provided herein, shall be limited to the fullest extent permitted by the amended DGCL. No amendment to or repeal of this Article VI shall apply to or have any effect on the liability or alleged liability of any director for or with respect to any acts or omissions of such director occurring prior to the effective date of such amendment or repeal.

Article VI The Corporation shall indemnify, advance expenses, and hold harmless, to the fullest extent permitted by applicable law as it presently exists or may hereafter be amended, any person (a “Covered Person”) who was or is made or is threatened to be made a party in any action, suit, or proceeding, whether civil, criminal, administrative, or investigative (a “Proceeding”), by reason of the fact that the Covered Person, or a person for whom the Covered Person is the legal representative, is or was a director, officer, or employee of the Corporation or, while a director, officer, or employee of the Corporation, is or was serving at the request of the Corporation as a director, officer, or employee of another corporation, partnership, joint venture, trust, enterprise, or nonprofit entity, including service with respect to employee benefit plans, against all liability and loss suffered and expenses (including attorneys’ fees) actually and reasonably incurred by such Covered Person. Notwithstanding the preceding sentence, the Corporation shall be required to indemnify a Covered Person in connection with a Proceeding (or part thereof) commenced by such Covered Person only if the commencement of such Proceeding (or part thereof) by the Covered Person was authorized in the specific case by the board of directors of the Corporation. Any amendment, repeal or modification of this Article VI shall not adversely affect any right or protection hereunder of any person in respect of any act or omission occurring prior to the time of such repeal or modification. Article VII Any action required or permitted to be taken by the stockholders of the Corporation may be taken only at a duly called annual or special meeting of the stockholders, and no action may be taken by the written consent of stockholders. Article VIII In furtherance and not in limitation of the powers conferred by the laws of the State of Delaware, the Board is expressly authorized to make, adopt, amend, alter and repeal the by-laws of the Corporation. The effective time of this Certificate of Incorporation shall be 5 p.m. Eastern time on May 4, 2026.

The undersigned hereby acknowledges that the foregoing Amended and Restated Certificate of Incorporation is his act and deed on this 4th day of May, 2026. By: /s/ Robert.S. Lowenthal Name: Robert S. Lowenthal Title: Chief Executive Officer and President

EX-99.1

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opy2026shareholdermeetin

Oppenheimer Holdings Inc. New York, NY May 4, 2026 Annual Stockholders' Meeting

WELCOME to Oppenheimer's 2026 Annual Stockholders' Meeting May 4, 2026 2

Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. These forward-looking statements may relate to such matters as anticipated financial performance, future revenues or earnings, business prospects, new products or services, anticipated market performance and similar matters. The Private Securities Litigation Reform Act of 1995 provides a safe harbor for forward-looking statements. Forward-looking statements are neither historical facts nor assurances of future performance. Instead, they are based only on the company’s current beliefs, expectations and assumptions regarding the future of the company’s business, future plans and strategies, projections, anticipated events and trends, the economy and other future conditions. Because forward-looking statements relate to the future, they are subject to inherent uncertainties, risks and changes in circumstances that are difficult to predict and many of which are outside of the company’s control. The company cautions that a variety of factors could cause the company’s actual results to differ materially from the anticipated results or other expectations expressed in the company’s forward-looking statements. These risks and uncertainties include, but are not limited to, those risk factors discussed in Part I, “Item 1A. Risk Factors” of our Annual Report on Form 10-K for the year ended December 31, 2025 filed with the Securities and Exchange Commission (the “SEC”) on February 26, 2026 (the “2025 10-K”) and Quarterly Report on Form 10-Q for the quarter ended March 31, 2026 filed with the SEC on May 1, 2026 (the “2026 10-Q1”). In addition, important factors that could cause actual results to differ materially from those in the forward-looking statements include those factors discussed in Part I, “Item 2. Management’s Discussion & Analysis of Financial Condition and Results of Operations” of the 2026 10-Q1. Any forward-looking statements herein are qualified in their entirety by reference to all such factors discussed in the 2025 10-K, the 2026 10-Q1 and the company’s other SEC filings. There can be no assurance that the company has correctly or completely identified and assessed all of the factors affecting the company’s business. Therefore, you should not rely on any of these forward-looking statements. Any forward-looking statement made by the company in this presentation is based only on information currently available to the company and speaks only as of the date on which it is made. The company does not undertake any obligation to publicly update or revise any forward-looking statements, whether written or oral, that may be made from time to time, whether as a result of new information, future developments or otherwise. 3

(1) Chart does not include $11.4 million allocated to Corporate/Other. (2) Represents book value less goodwill and intangible assets divided by number of shares outstanding. (3) Non-GAAP measures exclude a $70 million (pre-tax) accrual related to the "cash sweep" litigation settlement and $22.3 million (pre-tax) expense associated with the mark-to-market remeasurement of liability-based stock appreciation rights. Refer to the schedule on p. 16-17 for additional explanation of non-GAAP financial measures and a reconciliation of adjusted earnings per share to U.S. GAAP. (4) Attributable to Oppenheimer Holdings Inc. (5) Calculated using annualized dividends of $0.80 per share Business Overview Oppenheimer Snapshot (NYSE:OPY) 3/31/2026 12/31/2025 Stockholders' Equity ($M):(4) $952.4 $983.8 Market Cap ($M): $955.01 $760.56 Book Value per Share:(4) $88.95 $93.81 Tangible Book Value per Share:(2)(4) $72.28 $76.78 Share Price: $89.19 $72.29 (Loss) Earnings per Share (Basic):(4) $(1.93) $14.13 Adjusted Basic Earnings per Share (Basic) (Non- GAAP):(3)(4) $4.46 N/A (Loss) Earnings per Share (Diluted):(4) $(1.93) $13.04 Adjusted Earnings per Share (Diluted) (Non- GAAP):(3)(4) $4.21 N/A P/E Ratio (TTM): 9.62 5.12 Dividend Yield:(5) 0.90 % 1.00 % Employees: 2,958 2,947 # of Financial Advisors: 932 924 Retail Branches in the US: 88 88 Client Assets under Administration ($B): $139.8 $143.3 Client Assets Under Management ($B): $54.1 $55.2 A Preeminent Wealth Manager and Investment Bank Wealth Management Private client services and asset management solutions tailored to individuals' unique financial objectives Capital Markets Investment banking services and capital markets products for institutions and corporations Business Mix - FY 2025 Revenue ($1,638.1M)(1) 4 36% 64% Oppenheimer is a leading investment bank and full-service investment firm that provides financial services and advice to high net worth investors, individuals, businesses and institutions.

• Hong Kong, China• London, UK • Geneva, Switzerland • St. Helier, Isle of Jersey • Tel Aviv, Israel Global Footprint Strong presence in the U.S. and internationally • 88 retail branches in the U.S. • 5 international offices • 2,958 employees − 932 financial advisors − 165+ institutional sales professionals − 35+ senior research analysts US London Hong Kong Tel Aviv Geneva St. Helier Wealth Management Institutional Equities Fixed Income Investment Banking Research Data as of March 31, 2026 5

Summary Operating Results: 2025 vs 2024 (Unaudited) 6 Highlights ($000’s, except otherwise indicated) For the 12-Months Ended REVENUE 12/31/2025 12/31/2024 % Change Commissions $ 464,415 $ 409,710 13.4 % Advisory fees 555,439 483,433 14.9 % Investment banking 266,392 176,447 51.0 % Bank deposit sweep income 114,811 138,770 (17.3)% Interest 152,982 135,537 12.9 % Principal transactions, net 50,214 54,684 (8.2)% Other 33,818 33,915 (0.3)% Total Revenue 1,638,071 1,432,496 14.4 % EXPENSES Compensation and related expenses 1,016,506 936,814 8.5 % Non-compensation related expenses 410,374 389,925 5.2 % Total Expenses 1,426,880 1,326,739 7.5 % Pre-tax income 211,191 105,757 99.7 % Net income attributable to Oppenheimer Holdings Inc. $ 148,403 $ 71,557 107.4 % Earnings per share (Basic)1 $ 14.13 $ 6.91 104.5 % Earnings per share (Diluted)1 $ 13.04 $ 6.37 104.7 % 1 Attributable to Oppenheimer Holdings Inc. Record high revenue of $1.6 billion, basic earnings per share of $14.13 and diluted earnings per share of $13.04 Improved results in the Wealth Management segment driven by record high full year retail commissions and record high full year advisory fees attributable to a rise in billable AUM and an increase in incentive fees Profitable results in the Capital Markets segment driven by increased investment banking activity in addition to higher sales and trading revenue Compensation expenses increased from the prior year largely as a result of higher production- related expenses and incentive compensation accruals Returned value to shareholders by declaring a $1.00 per share special dividend payable in January 2026 while repurchasing 46,292 shares during the year at an average price of $64.36 per share The effective tax rate for the 2025 year improved to 29.9% compared with 32.6% for the prior year as the impact of certain unfavorable permanent items and nondeductible foreign losses was reduced due to higher income levels

The effective tax rate for the current period was 23.8%, slightly lower when compared with 25.9% for the prior year period due to the impact of a discrete legal charge related to the "cash sweep" settlement recorded during the quarter Summary Operating Results: 1Q-26 vs 1Q-25 (Unaudited) Highlights ($000’s, except otherwise indicated) For the 3-Months Ended REVENUE 3/31/2026 3/31/2025 % Change Commissions $ 128,341 $ 110,878 15.7 % Advisory fees 141,718 128,803 10.0 % Investment banking 97,720 47,623 105.2 % Bank deposit sweep income 26,118 30,075 (13.2) % Interest 37,531 36,369 3.2 % Principal transactions, net 10,787 8,975 20.2 % Other 2,880 5,102 (43.6)% Total Revenue 445,095 367,825 21.0 % EXPENSES Compensation and related expenses(2) 296,001 227,091 30.3 % Non-compensation related expenses(3) 176,095 99,358 77.2 % Total Expenses 472,096 326,449 44.6 % Pre-tax (loss) income (27,001) 41,376 (165.3)% Net (loss) income attributable to Oppenheimer Holdings Inc. $ (20,578) $ 30,655 (167.1)% (Loss) Earnings per share (Basic) 1 $ (1.93) $ 2.93 (165.9)% (Loss) Earnings per share (Diluted) 1 $ (1.93) $ 2.72 (171.0)% Higher revenue for the first quarter of 2026 was driven by significantly higher investment banking fees, increased transaction-based commissions and greater advisory fees reflecting growth in billable assets under management (“AUM”) Assets under management and administration both increased year-over-year as of March 31, 2026, primarily due to market appreciation Compensation expenses rose from the prior year quarter due mainly to elevated costs associated with stock appreciation rights2 tied to the Company's share price, higher production- related costs and greater incentive compensation accruals Non-compensation expenses significantly increased from the prior year quarter primarily due to legal costs associated with our settlement of the "cash sweep" class action litigation3 The Board of Directors increased the quarterly dividend to be paid on May 29, 2026 by 11.1% to $0.20 per common share 7 1 Attributable to Oppenheimer Holdings Inc. 2 During the quarter-ended March 31, 2026, the Company incurred a $22.3 million (pre-tax) expense associated with a recurring liability- based employee compensation award program for financial advisors that are tied to our stock price. 3 During the quarter-ended March 31, 2026, the Company incurred a $70 million (pre-tax) expense associated with a legal accrual for the settlement of the "cash sweep" class action litigation.

8 Select Financial Measures Earnings (Loss) per Share ("EPS") ($)1 Net Income (Loss) ($M)1Revenue ($M) Stockholders’ Equity ($M)1 1 Attributable to Oppenheimer Holdings Inc. 2 Non-GAAP measure excludes a $70 million (pre-tax) accrual related to the "cash sweep" litigation settlement and $22.3 million (pre-tax) expense associated with the mark-to-market remeasurement of liability-based stock appreciation rights. Refer to the schedule on p. 16-17 for additional explanation of non-GAAP financial measures and a reconciliation of adjusted net income and adjusted earnings per share to U.S. GAAP. 2 1Q-26 Adjusted EPS 2

9 OPY Historical Stock Price $106.81 NYSE: OPY May 1, 2026 Da ily V ol um e OPY Class A stock price change after March 31, 2026 (through April 28th) $89.19 closing price on March 31, 2026

10 Capital Structure Book Value & Tangible Book Value per Share ($) Dividends and Stock Repurchases As of March 31, 2026 ($ in thousands) Total Assets: $ 3,815,278 Stockholders’ Equity:(1) $ 952,426 Broker-Dealer Regulatory Capital ($ in millions) Regulatory Net Capital: $ 437.2 Regulatory Excess Net Capital: $ 403.9 88.95 72.41 76.72 82.31 93.81 82.87 Average Short-term Borrowings • The Board of Directors announced a $0.02 or 11.1% increase in the quarterly dividend to $0.20 per share effective for the first quarter of 2026 payable on May 29, 2026 to holders of Class A non-voting and Class B voting common stock of record on May 15, 2026 • There were no OPY Class A stock repurchases during the quarter ended March 31, 2026 (1) Attributable to Oppenheimer Holdings Inc.

11 Interest and Fee Revenue Margin Lending Interest and Fee Revenue ($M) • Client funds swept into deposit accounts at participating banks and eligible for FDIC deposit insurance • 50+ participating banks • FDIC-Insured Bank Deposit program had a balance of $3.0 billion at 3/31/26 • Bank deposit sweep income of $110.9 million for TTM 3/31/26 FDIC-Insured Bank Deposit Program • Credit extended to clients on a collateralized basis • Average customer margin debits were $1.4 billion for TTM 3/31/26 • Margin interest revenue of $85.4 million for the TTM 3/31/26

Leading Wealth Management Platform Well-recognized brand and one of the few independent, non-bank broker-dealers with full service capabilities Retail Services • Full-Service Brokerage • Financial Planning, Retirement Services, Insurance Solutions, Corporate & Executive Services & Trust Services • Margin & Securities Lending Advisory Services • Investment Policy Design & Implementation • Asset Allocation & Portfolio Construction • Research, Diligence & Manager Selection • Portfolio Monitoring & Reporting Alternative Asset Management • Hedge Funds & Fund-of-Funds • Private Equity Wealth Management Services Wealth Management Revenue ($M) Client Assets per Financial Advisor ($M) Wealth Management Pre-Tax Profit Margin 12 1 1 Adversely impacted by a $22.3 million (pre-tax) expense associated with stock appreciation rights

Wealth Management Metrics Sustained shift to Fee-Based Revenue Advisory Fees as a Percentage of Wealth Management Advisory Fees and Commissions Client Assets Under Administration ($B) Client Assets Under Management ($B) 13

18.4% Sales & Trading Revenues 2025 vs 2024 56.2% Investment Banking Revenues 2025 vs 2024 Capital Markets A leading capital markets business providing sophisticated investment banking, research and trading solutions Healthcare Technology Transportation & Logistics Financi l Institutions Consumer & Retail Industrials & Energy Capital Markets Revenue Breakdown 2025 Capital Markets Revenue ($M) Investment Banking Focus IndustriesInstitutional Equities • Sales and Trading • Equity Research − 36 senior research analysts covering ~675 companies • Corporate Access (Conferences & NDRs) Investment Banking • Mergers & Acquisitions • Equity Capital Markets • Debt Capital Markets • Restructuring & Special Situations Fixed Income • Taxable Fixed Income Sales & Trading • Non-Taxable Fixed Income Sales & Trading • Public Finance Eq ity Services 2025 $591.3M 14 $32.7 5%

Summary Investing in our future and poised for growth Technology Transportation & Logistics Energy 15 In Review Looking Forward In 2025, we achieved record revenue and EPS, driven by near-record Capital Markets revenue from increased investment banking activity and strong Wealth Management performance from record commissions and advisory fees Our solid capital position afforded us the ability to return capital to stockholders through a $1.00 per share special dividend payable in January 2026 while repurchasing 46,292 Class A non- voting common shares in 2025 Well-positioned to advise clients amid heightened macroeconomic uncertainty, evolving monetary policy, and a complex geopolitical landscape that continues to drive market volatility Will continue to pursue organic and inorganic growth opportunities in areas complimentary to our existing businesses while continuing to look at the independent channel and other strategic partnerships Moving into Q2-2026, we continue to moni or the geopolitical uncertainty, including escalati n ten ions involving Iran, and its potential impact on trade flows, market conditions, client activity and capital formation We are experiencing unprecedented demand for intern and analyst positions, which–together with selective hiring of qualified, experienced candidates—strengthens our long-term talent pipeline In Q1 2026, our core operating businesses built on the prior year's momentum, delivering strong segment performance with multiple contributors to year-over- year revenue growth We continued to strengthen our brand by refining and relaunching The Power of Oppenheimer Thinking campaign in Q1 2026, alongside repositioning our media strategy based on 2025 performance insights

Net (Loss) Income Attributable to Oppenheimer Holdings Inc. and (Loss) Earnings Per Share U.S. GAAP Reconciliation For the Three Month Ended March 31, 2026 For the Three Month Ended March 31, 2025 Net (loss) income attributable to Oppenheimer Holdings Inc. (U.S. GAAP) $ (20,578) $ 30,655 Non-GAAP adjustments: Class action sweep litigation settlement $ 70,000 $ — Liability-based stock appreciation rights expense $ 22,285 $ (2,742) Tax impact of Non-GAAP adjustments (1) $ (24,216) $ 714 Adjusted net income attributable to Oppenheimer Holdings Inc. (Non-GAAP) $ 47,491 $ 28,627 Basic (loss) earnings per share (U.S. GAAP) $ (1.93) $ 2.93 Impact of Non-GAAP adjustments $ 6.39 $ (0.19) Adjusted basic earnings per share (Non-GAAP) $ 4.46 $ 2.74 Diluted (loss) earnings per share (U.S. GAAP) $ (1.93) $ 2.72 Impact of Non-GAAP adjustments $ 6.14 $ (0.18) Adjusted diluted earnings per share (Non-GAAP) $ 4.21 $ 2.54 Weighted average share outstanding Basic (U.S. GAAP and Non-GAAP) 10,642,909 10,465,771 Diluted (U.S. GAAP) 10,642,909 11,277,939 Diluted (Non-GAAP) (2) 11,288,897 11,277,939 ('000s, except per share amounts) Reconciliation of net (loss) income attributable to Oppenheimer Holdings Inc. to adjusted net income attributable to Oppenheimer Holdings Inc., reconciliation of basic (loss) earnings per share to adjusted basic earnings per share, and reconciliation of diluted (loss) earnings per share to adjusted diluted earnings per share are as follows: (1) The tax impact is estimated using the statutory rates for the applicable entities (2) Includes 645,988 shares which were previously anti-dilutive due to the net loss, however, the Non-GAAP adjustments result in adjusted net income and those shares are now dilutive 16

Explanation of Non-GAAP Financial Measures The Company included certain non-GAAP financial measures within this presentation to supplement the U.S. Generally Accepted Accounting Principles ("GAAP") financial information. Adjusted results begin with information prepared in accordance with U.S. GAAP, and such results are adjusted to exclude, or include, certain items. Specifically, we included non-GAAP measures that adjust the Company’s net income and earnings per share to exclude the expense associated with the settlement of the class action “cash sweep” litigation because management does not view this as ordinary-course litigation for the Company given the nature of the claims and the manner in which the action was brought. We also included non-GAAP measures that exclude compensation expense related to the recurring, mark-to-market remeasurement of liability-based stock appreciation rights from net income and earnings per share because the period-to-period variability in this expense is largely driven by factors outside the Company’s direct control, including changes in the fair value of and underlying volatility levels in Oppenheimer Holdings Inc.’s Class A common stock price. For this reason, management expects to provide this non-GAAP measure in future reporting periods, subject to ongoing evaluation. The Company believes that these non-GAAP financial measures provide additional useful information for investors because they permit investors to view the Company's financial performance measures on a basis consistent with how management views the operating performance of the Firm. These non-GAAP financial measures, when presented in conjunction with comparable U.S. GAAP measures, are also useful to investors when comparing the Company’s results across different financial reporting periods on a consistent basis. The tables on the previous slide reconcile our non-GAAP financial measures to their respective U.S. GAAP measures. These non- GAAP financial measures have limitations as analytical tools and should not be considered in isolation from, as a substitute for, or superior to, the analysis of U.S. GAAP financial measures. 17

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