Which of the many talented fillies taking aim at the 2025 Longines Kentucky Oaks is most likely to visit the winner’s circle May 2 at Churchill Downs?

History can guide us toward the answer in this marquee Grade 1 race for 3-year-old fillies. Reviewing the last 20 editions of the Kentucky Oaks reveals eight recurring trends you can use to sort through the contenders:

Early speed is an advantage

The pace of the Kentucky Oaks is typically modest — the fastest half-mile fraction of the past 20 years is :46.24, and the fastest six-furlong split is 1:11.25. As a result, early speed is typically an asset in the Kentucky Oaks. Nine of the last 20 winners were first or second after the opening half-mile, and 15 of the last 20 were positioned in the top five.

Favor fillies who prepped at Fair Grounds

Nine of the last 20 Kentucky Oaks winners ran at least once at Fair Grounds leading up to the Kentucky Oaks. That includes eight fillies who competed the Grade 2 Fasig-Tipton Rachel Alexandra Stakes and seven fillies who ran in the Grade 2 Fasig-Tipton Fair Grounds Oaks. Note: The Rachel Alexandra Stakes was previously the Silverbulletday Stakes before it was renamed in 2011 in honor of the 2009 Horse of the Year.

Longshots often finish in the top three

2023 Kentucky Oaks upset winner Pretty Mischievous (Eclipse Sportswire)

Did you know 23 out of 60 Kentucky Oaks trifecta finishers since 2005 (38%) started at double-digit odds? That averages out to slightly more than one per year, and the group includes six double-digit longshots (Lemons Forever, Believe You Can, Princess of Sylmar, Serengeti Empress, Shedaresthedevil, and Pretty Mischievous) who finished first.

Bet on graded stakes winners

Proven graded stakes winners perform best in the Kentucky Oaks. They’ve won 17 of the last 20 editions.

Post positions 10-14 have been advantageous

Fillies drawn in post positions 10 and wider outperform those drawn in posts 1-9. Since 2005, 20 out of 73 fillies (27%) starting from double-digit posts have recorded top-three finishes in the Kentucky Oaks, compared with 40 out of 176 fillies (23%) starting from posts 1-9.

Avoid fillies breaking from post positions 1 and 2

Post positions 1 and 2 are detrimental in the Kentucky Oaks. While Secret Oath managed to win from the rail post, she’s one of only two fillies in the last 20 years to crack the Kentucky Oaks trifecta from post 1. During the same timeframe, post 2 has produced only four top-three finishers.

Favor fillies who contested one or two prep races

There’s a developing trend for Kentucky Oaks winners to run in only one or two races as 3-year-olds in advance of the Oaks. Not counting 2020 (when the Kentucky Oaks was delayed until September due to COVID-19), six of the last seven winners have taken the one- or two-prep approach, compared with only one out of 12 winners from 2005-2016.

Avoid betting fillies based in California

California-based fillies, including Rags to Riches, Blind Luck, and Plum Pretty, used to win the Kentucky Oaks on a regular basis. But that hasn’t been the case in recent years. Only one Oaks winner in the last 13 years (Abel Tasman) has come out of California.

Conclusions

Good Cheer, a multiple stakes winner at Fair Grounds (Eclipse Sportswire)

Pending the post-position draw, history suggests the most likely winner of the 2025 Kentucky Oaks is Good Cheer, a proven graded stakes winner with strong Fair Grounds form under her belt.

Good Cheer has run twice this year, dominating the Fasig-Tipton Rachel Alexandra Stakes and Fasig-Tipton Fair Grounds Oaks. And while she’s not a pacesetter by any means, Good Cheer has some degree of early speed and usually races within 1 1/2 to three lengths of the pace. There’s a decent chance she’ll be positioned in the first five at the half-mile mark of the 2025 Kentucky Oaks.

Assuming Good Cheer draws a favorable post position (ideally post 10 or wider, and definitely not posts 1 or 2), bettors can feel confident supporting this Godolphin homebred to win.

Good luck with your handicapping!