This contest is expired. Please use the site navigation to find active contests.

Win Horse Sweepstakes Contests min
enter contest

Kentucky Derby of a Lifetime Sweepstakes

The Kentucky Derby of a Lifetime Sweepstakes will award one Grand Prize Winner a trip for 2 to the Kentucky Oaks and Kentucky Derby in Louisville, Kentucky. The Win a Vacation Sweepstakes Prize Package includes: airfare; 3 night hotel stay; race tickets; tickets to Taste of Derby; select ground transportation; Clothing; Headwear; Paddock visit; Backside visit; Woodford Reserve Distillery visit; and Kentucky Derby Red Carpet.

10 First Prizes: A Kentucky Derby gift pack. ARV: $100.

  • Grand Prize:   A trip for 2 to the Kentucky Derby and Kentucky Oaks in Louisville, KY - includes airfare, 3 night hotel stay, tickets to Taste of Derby, & more!
  • ARV: $36,600
  • Total ARV: $37,600
  • Company: Churchill Downs Racetrack, LLC
  • Eligibility: Legal Residents of the 50 U.S., D.C., Canada (void in Quebec), UK, Ireland, Japan, and continental France, ages 21 or older
  • Start Date: 03/31/2023
  • Deadline Date: 01/31/2024
  • Entry Fee: $0
  • Frequency: daily


start winning today!

See how to maximize your winning potential and unlock exciting features designed to help you win.

Get Started
Beach Lounge