WINS-Day Challenge sponsored by Malone's

Wednesdays in October

Each Wednesday during live racing, Keeneland offers the WINS-Day Challenge handicapping contest, which has a $2,500 guaranteed pool. Enter the contest for $10 at Wagering Central (located on the first floor of the Grandstand) and place a mythical $2 win and place wager – that means no actual money is required – on Keeneland races 3 through 8.


Participating in the WINS-Day Challenge is an inexpensive way for beginning handicappers to test their skills and is a great way for fans to give handicapping contests a try. Inexperienced bettors can and do win.

The contest awards the winner $1,250 with money distributed through 10th place. Limit three entries per person.

View Oct. 9 Results

View Oct. 23 Results