Notice of Annual Meeting of Shareholders 2021 Proxy Statement 2020 Annual Report on Form 10-K Chairman and CEO’s Message Dear Fellow Shareholders, Our country faced unprecedented challenges in 2020 stemming from the COVID-19 global pandemic. Our leadership teams’ quick actions to reduce our cost structure, preserve capital and provide additional financial resources in response to this crisis reflected the resilience necessary to weather these difficult times. We are proud of how our leadership team and our team members reacted quickly to the pandemic’s threat to our company and we want to personally thank each of them for their commitment and dedication. Their actions enabled our properties to reopen safely for our team members, our guests, and our communities. In 2020, despite the adversity that our team faced, our portfolio of businesses still generated over $1 billion of revenue and $287 million of Adjusted EBITDA. Also, we had a total shareholder return in 2020 of 43%—a return that significantly exceeded the S&P 500, the Russell 2000, and the S&P Midcap 400 Index. We are especially proud of the following 2020 accomplishments: Š In a very challenging environment, we safely ran the 146th Kentucky Derby, spectator-free on the first Saturday of September, generating double digit positive EBITDA. We protected the safety of our community and team members and also protected the reputation, the brand, and the long-term value of this iconic asset. Š Our TwinSpires Horse Racing business delivered record revenue and Adjusted EBITDA. Š The margin for our wholly-owned casino properties in the second half of 2020 was up 690 basis points excluding quarterly results for properties that were closed during this period. Š We now have three historical racing machine (HRM) facilities that have generated nearly 600 full-time equivalent jobs for Kentucky and generated substantial purse money for Kentucky’s racetracks which in turn fuels the entire Kentucky horse industry. – Our Derby City Gaming business generated more Adjusted EBITDA in 2020 than in 2019 despite being closed for approximately 100 days in 2020. – We opened our Oak Grove Racing, Gaming & Hotel Facility including a hotel in southwest Kentucky, in mid- September 2020 and we opened our Newport Racing and Gaming Facility in Newport, Kentucky in October 2020. 2021 is a transition year for our company. We have already begun to reinvigorate our organic growth plans: Š We remain committed to protecting and building our iconic asset—The Kentucky Derby. We will announce an updated expansion plan for Churchill Downs Racetrack. Š We are building our Turfway Park HRM facility. Š We will further invest in and grow our Derby City Gaming, Oak Grove and Newport properties. Š We are building an expansion at Rivers Casino Des Plaines. Š We will remain disciplined in growing our TwinSpires Horse Racing business—the most profitable online wagering platform - and building a long-term profitable TwinSpires Sports and Casino business. Š We will remain focused on maintaining safety and health protocols as we efficiently grow our gaming properties and acquire strategic gaming properties at reasonable multiples. We remain thoughtful stewards of our shareholders’ capital and will invest capital to create long-term shareholder value while maintaining capacity for dividend growth and opportunistic share repurchases. We are well-positioned to capitalize on our growth pipeline as we return to lower leverage levels. We look forward to our businesses returning to full throttle, accelerating the growth from our newer properties, and executing our organic growth opportunities over the coming years. R. Alex Rankin Chairman of the Board William C. Carstanjen Chief Executive Officer Financial Highlights FINANCIAL HIGHLIGHTS $ in millions, except per share data 2018 2019 2020 Consolidated Financial Results Net revenue $ 1,009 $ 1,330 $ 1,054 Operating income $ 189 $ 216 $ 60 Net income from continuing operations $ 183 $ 140 $ 13 Diluted EPS from continuing operations $ 4.39 $ 3.44 $ 0.33 Adjusted EBITDA1 $ 328.8 $ 451.4 $ 286.5 Consolidated Balance Sheet Total Assets $ 1,725 $ 2,551 $ 2,686 Total Debt $ 884 $ 1,474 $ 1,622 Total Liabilities $ 1,252 $ 2,040 $ 2,319 Shareholders’ Equity $ 473 $ 511 $ 367 Cash Flow and Liquidity Cash Flows from Operating Activities $ 198 $ 290 $ 142 Capital Maintenance Expenditures $ 30 $ 48 $ 23 Net Leverage Ratio2 2.3x 3.1x 5.4x Shareholder Data: Dividends Declared per Common Share $ 0.543 $ 0.581 $ 0.622 Common Stock Share Repurchases $ 532 $ 93 $ 28 Year-End Closing Stock Prices $ 81.31 $ 137.20 $ 194.79 Equity Market Capitalization $ 3,285 $ 5,446 $ 7,690 Total Capitalization $ 4,169 $ 6,920 $ 9,312 TOTAL SHAREHOLDER RETURN(3) 1 Year 3 Year 5 Year 155% 325% 43% 49% 103% 79% 86% 18% 14% 20% 28% 34% S&P S&P Midcap Russell CHDN S&P S&P Midcap Russell CHD S&P S&P Midcap Russell CHDN 500 400 2000 500 400 2000 500 400 2000 1 Please refer to “Item 7 Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Company’s Form 10-K for the fiscal year ended December 31, 2020 filed with the SEC on February 24, 2021 for a discussion of Adjusted EBITDA, a non-GAAP financial measure, and a reconciliation to the most directly comparable GAAP measure. 2 Net leverage ratio is the ratio of total debt (less cash) to Adjusted EBITDA. 3 Total Shareholder Return (“TSR”) assumes dividends are reinvested. One year TSR is calculated from December 31, 2019 to December 31, 2020. Three year TSR is calculated from December 31, 2017 to December 31, 2020. Five year TSR is calculated from December 31, 2015 to December 31, 2020. 600 N. HURSTBOURNE PARKWAY,STE. 400 LOUISVILLE,KENTUCKY 40222 NOTICE OF ANNUAL MEETING OF SHAREHOLDERS DATE AND TIME: Tuesday, April 20, 2021, at 9:00 a.m. Eastern Time PLACE: Via a live audio-only webcast at www.proxydocs.com/CHDN. There is no physical location for the 2021 Annual Meeting. I. To elect the three (3) Class I Directors identified in this Proxy Statement for a term of three (3) years (Proposal No. 1); II. To ratify the appointment of PricewaterhouseCoopers LLP as the Company’s independent AGENDA: registered public accounting firm for fiscal year 2021 (Proposal No. 2); III. To conduct an advisory vote to approve executive compensation (Proposal No. 3); and IV. To transact such other business as may properly come before the meeting or any adjournment thereof, including matters incident to its conduct. The close of business on March 1, 2021, has been fixed as the record date for determining the RECORD DATE: shareholders entitled to notice of, and to vote at, the Annual Meeting. Only shareholders of record at that time will be entitled to notice of and to vote at the Annual Meeting and at any adjournments thereof. To attend and vote during the Annual Meeting visit www.proxydocs.com/CHDN. All shareholders, including those who expect to attend the Annual Meeting virtually, are urged to vote prior to the Annual Meeting by telephone or Internet or by requesting and promptly VOTING: signing and returning a proxy card, as more fully described in the Notice of Internet Availability of Proxy Materials. March 11, 2021 By Order of the Board of Directors. BRADLEY K. BLACKWELL Senior Vice President, General Counsel and Secretary IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON APRIL 20, 2021 The Company’s Proxy Statement for the 2021 Annual Meeting of Shareholders and the Annual Report to Shareholders for the fiscal year ended December 31, 2020 are available at http://www.churchilldownsincorporated.com/proxy Table of Contents TABLE OF CONTENTS Notice of Annual Meeting of Shareholders 2020 “Say-on-Pay” Advisory Vote on Executive Compensation .... 29 Role of Management and Independent Advisors ............. 29 Factors Used to Evaluate Pay Decisions .................... 30 Proxy Statement 1 Non-Disclosure of Certain Metrics and Targets .............. 31 Annual Meeting of Shareholders to be held on April 20, 2021 . 1 Components of Compensation ........................... 32 VotingRights......................................... 1 Base Salary ........................................... 32 Voting Instructions and Information ....................... 2 Executive Annual Incentive Plan .......................... 33 Security Ownership of Certain Beneficial Owners and Financial Component (75%) ............................. 33 Management ........................................ 5 Qualitative Component (25%) ........................... 34 Information about our Executive Officers ................... 8 Summary of 2020 EAIP Awards ........................... 35 Long-Term Incentives .................................. 36 Election of Directors (Proposal No. 1) 9 Executive Stock Ownership Guidelines ..................... 38 Anti-Hedging Policy .................................... 39 Election of Directors ................................... 10 Clawback Policy ....................................... 39 Continuing Directors ................................... 11 Deferred Compensation and Other Benefits ................ 39 Retirement Age Policy .................................. 12 Compensation Committee Report ........................ 40 Emeritus Directors ..................................... 13 Director Compensation for Fiscal Year Ended December 31, 2020 . 13 2020 Summary Compensation Table 41 Director Stock Ownership Guidelines ...................... 14 Corporate Governance 16 All Other Compensation for Fiscal