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As the official betting partner of the Kentucky Derby, TwinSpires partnered with Chalkline to power the Kentucky Derby Freeplay Challenge. For a third consecutive year, horse racing fans can win up to $1,000,000 when they answer 15 questions about the event.

“The Kentucky Derby is the biggest event of the year for many sports fans, bettors and gaming enthusiasts.” said Chalkline CEO Daniel Kustelski. “Chalkline is thrilled to power the TwinSpires Kentucky Derby Challenge for a third consecutive year and continue a tradition of delivering an exciting chance for racing fans to win big.”

How To Win

Visit the TwinSpires site to participate in the freeplay challenge. You do not need to create an account to qualify; however, you do need to be a US resident, accept the terms and conditions, and provide your email. You also need to be at least 21 years old.

Among other questions and selections, the TwinSpires Freeplay Challenge will have contestants:

  • Pick the winning horse
  • Pick the third-place finisher
  • Select the winning time
  • Choose the winner of head-to-head matchups

Whether you know horse racing inside and out or choosing at random, anyone could win the million-dollar prize.

About TwinSpires And Chalkline


TwinSpires is a top-tier horse race betting site available in most states in the US. New players can receive a 100% deposit match up to $200 with code GET200. Terms and conditions apply.

TwinSpires Sportsbook is also available in Colorado, Indiana, Michigan, New Jersey, and Pennsylvania. The app incorporates both sports betting and horse racing. In all states except Colorado and Indiana, TwinSpires Sportsbook also offers casino games.


Chalkline provides real-money and freeplay games for operators across the US and abroad. Products include casino gaming leaderboards, fantasy sports contests, online lotteries, and novelty games like Oscars contests.

About the Author
Mike Epifani

Mike Epifani

Casino Content Manager
Mike Epifani is a gambling expert and professional writer. His current role is Brand Content Manager at, part of the Catena Media network. Mike spoke on the affiliate marketing panel at G2E 2022 in Las Vegas and won "Casino Affiliate of the Year" at the 2022 SBC Awards North America in NYC.

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