DraftKings Inc.

Securities Trading Plans of Directors and Executive Officers

Certain of our directors and executive officers have made, and may from time to time enter into trading plans or make elections to have shares sold or withheld to cover withholding taxes or pay the exercise price of options, which may be designed to satisfy the affirmative defense conditions of Rule 10b5-1 under the Exchange Act or may constitute non-Rule 10b5-1 trading arrangements (as defined in Item 408(c) of Regulation S-K).

On September 9, 2025, Matthew Kalish, our President, DraftKings North America and a member of our Board of Directors, entered into a trading agreement designed to satisfy the affirmative defense conditions of Rule 10b5-1 under the Exchange act (the “Kalish 10b5-1 Plan”). The Kalish 10b5-1 Plan provides for the sale of up to 1,260,000 shares of the Company's Class A common stock and terminates on March 3, 2026, or earlier if all transactions under such trading agreement are completed.

Matthew Kalish Transition

On November 6, 2025, Mr. Kalish and the Company mutually agreed that Mr. Kalish will transition out of his role as President, DraftKings North America, effective as of March 31, 2026 (the “Transition Date”). In connection with Mr. Kalish’s transition, the Company entered into a Transition Agreement with Mr. Kalish, pursuant to which Mr. Kalish will step down from all other roles as an officer or employee of the Company and any of its subsidiaries, effective as of the Transition Date. Mr. Kalish will remain a director on the Board of Directors of the Company after the Transition Date.

In recognition of, among other things, Mr. Kalish’s 14 years of service as a co-founder of the Company, subject to the terms and conditions of the Transition Agreement, (i) the performance-based restricted stock units (“PSUs”) that were granted in November 2022 and February 2023 with respect to performance in calendar year 2026 will accelerate and vest as of December 10, 2025 (the “Accelerated Vesting Date”), with performance deemed to be achieved at the maximum performance level (200%), (ii) outstanding time-based RSUs will continue vesting, under their original terms, through the last scheduled March 1, 2026 vesting date, (iii) PSUs that were granted in February 2024 with respect to performance in calendar year 2025 will continue vesting, under their original terms, through the filing of the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025 and (iv) vested stock options will remain outstanding subject to their terms. Other than as set forth above, all remaining equity awards that would have been outstanding and unvested as of the execution of the Transition Agreement were forfeited and cancelled as of November 6, 2025.

Pursuant to the Transition Agreement, Mr. Kalish will receive continued security services and payment of COBRA premiums until March 31, 2027. He also will receive director compensation in connection with his continued service on the Board of Directors.

The foregoing descriptions are qualified in their entirety by reference to the Transition Agreement, which is filed as Exhibit 10.1 to this Quarterly Report on Form 10-Q.