What is the Regret Stakes?
The Regret Stakes is a Grade III Thoroughbred race held annually at Churchill Downs in Louisville, Kentucky. Contested at 1⅛ miles on the Matt Winn Turf Course exclusively for 3-year-old fillies, it is the premier mid-distance turf test for sophomore fillies on the Churchill Downs Spring Meet calendar and a key benchmark for the top members of the division targeting summer championship events. The race is named in honor of Regret, Harry Payne Whitney's brilliant champion filly who became the first filly to win the Kentucky Derby in 1915, winning wire-to-wire in front of a crowd of 60,000. Voted the third greatest filly in American racing history by the American Trainers Association, Regret won all of her 11 starts at two and went undefeated as a two-year-old. Inaugurated in 1970 at six furlongs, the Regret Stakes has been contested at its current distance of 1⅛ miles on turf since 2003 and received Grade III status in 1999.
When is the Regret Stakes in 2027?
The 2027 Regret Stakes is scheduled for Saturday, May 30 at Churchill Downs. Contested at 1⅛ miles on the Matt Winn Turf Course with a purse of $275,000, the race draws the top 3-year-old turf fillies in the country targeting summer stakes including the Indiana Oaks and the Lake Placid Stakes at Saratoga.
Regret Stakes History & Notable Winners
Trainer Brad Cox delivered the most celebrated recent Regret Stakes performance when Fionn set the stakes record of 1:47.29 under Florent Geroux in 2025, breaking the 19-year-old mark of 1:47.31 set by Lady of Venice in 2006. Pin Up Betty gave trainer Mike Maker and jockey Luis Saez a 2024 win in 1:50.70, launching a campaign that would carry her to a stakes record in the Old Forester Mint Julep the following year. Mission of Joy gave trainer Graham Motion and jockey Tyler Gaffalione a 2023 score in 1:49.05 for Madaket Stables. Walkathon gave jockey Julien Leparoux his record fourth Regret Stakes win in 2022 under trainer Ian Wilkes in 1:49.26. Gam's Mission gave trainer Cherie DeVaux her first graded stakes win in 2021 under Adam Beschizza in 1:51.02, launching a career that would include the 2022 Mint Julep Stakes.
| Year | Winner | Jockey | Time |
|---|---|---|---|
| 2025 | Fionn | Florent Geroux | 1:47.29* |
| 2024 | Pin Up Betty | Luis Saez | 1:50.70 |
| 2023 | Mission of Joy | Tyler Gaffalione | 1:49.05 |
| 2022 | Walkathon | Julien Leparoux | 1:49.26 |
| 2021 | Gam's Mission | Adam Beschizza | 1:51.02 |
* Stakes record.
The Regret Stakes is the premier turf test for 3-year-old fillies on the Churchill Downs Spring Meet and one of the most important sophomore filly races on the summer racing calendar.
