Woodbine Challenge

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$2,000 Woodbine Challenge | September 16th   


It’s Woodbine Mile Day which features four graded stakes races including the $800,000 Ricoh Woodbine Mile Stakes.

Enter and play Woodbine for your chance to win a piece of the $2,000 prize pool!



  • Players will be required to deposit $50 into a Winners contest account to play.
  • Maximum three (3) entries.


Prize Structure:

$2,000 Guaranteed Prize Pool

  • 1st Place – $1,300
  • 2nd Place – $350
  • 3rd Place – $150
  • 4th Place – $125
  • 5th Place – $75


How to Enter:

Click here for a Venue application.

Click here for a Telebet application.


Where to Play:

Play at any Winners Venue in Connecticut or with Winners Telephone Betting.

For more information or to sign up, see a Winners team member at any Winners Venue or call Customer Care at 800.468.2260 (toll free).

Click here for a listing of Winners Venues in Connecticut.



ALL LIVE RACES on Saturday, September 16 originating from Woodbine; first post is 1:00 PM (EST).



  • Wager types: Win, Place & Show ONLY
  • Players must wager a minimum of $50 per account to be eligible for prize awards
  • Venue players will place event wagers through self-service machines
  • Telephone Betting players will place event wagers through a special one-day account


Additional Information:

  • If a tie exists, prize money will be equally divided among the players involved.



Click here to view the content leaderboard.

  • Leaderboard link will be enabled the day of the event.
  • Please note that it may take 2 to 5 minutes for the leaderboard to update after race results are official.


Quick Facts:

Click here to view our quick facts of the contest.



Click here to view the official rules of the contest.



Click here to view the September 16th results.


Terms and Conditions:

*Must be of legal wagering age to participate: 18+; 21+ at Winners Putnam & Winners Stamford. For additional information “See link for complete Official Rules” above.