Skip navigation
Sign up to follow your favorites on all your devices.
Sign up
NBCSports Header Logo

Pretty Mischievous holds off Gambling Girl to win the 2023 Kentucky Oaks

Brendan Walsh trainee Pretty Mischievous holds off a hard charging Gambling Girl to claim victory in the 149th Kentucky Oaks.

Pretty Mischievous, the 10-1 morning-line shot, showed her talent in the 2023 Kentucky Oaks (G1), holding off a hard-charging Gambling Girl to claim victory at Churchill Downs. The Kentucky Oaks is run at a distance of 1 1/8 miles at Churchill Downs with a purse of $1.25 million and is limited to 3-year-old fillies.

This is the first career Oaks win for trainer Brendan Walsh. Tyler Gaffalione was in the irons, picking up his first Oaks victory. He will ride Bob Baffert’s Medina Spirit in the Kentucky Derby.

Flying Connection, fielded by Todd Fincher and Florent Geroux, set the pace early. Pretty Mischievous settled comfortably in fifth place on the first turn. She found a clean lane around the final turn and started pulling away before Gambling Girl made a hard charge, nearly catching Pretty Mischievous at the wire.

“We always thought [Pretty Mischievous] was a very, very good filly,” Walsh told NBC Sports’ Kenny Rice right after the race. “We’re ecstatic for the whole team.”

Pretty Mischievous paid $22.74 to win, $10.10 to place and $7.40 to show. Gambling Girl (13-1), who took second, paid $12.84 to place and $8.36 to show. Third-place finisher The Alys Look (30-1) paid $13.60 to show.

All eyes turn to the 149th Kentucky Derby, where 3-year-old favorite Forte looks to stay undefeated in 2023 against a field of 18 other horses.

Watch the 149th running of the Kentucky Derby on Saturday, May 6 from 12 to 7:30 p.m. ET on NBC. Full coverage is also available on, the NBC Sports app and Peacock.