Analyzing the recent history of the Grade 1 Longines Kentucky Oaks can help us identify the most likely winner of the $1.5 million race May 1 at Churchill Downs.

Below are seven historical trends and tendencies common among past Kentucky Oaks winners. In previous analyses on America’s Best Racing, we’ve used these trends to identify two of the last three Kentucky Oaks winners: Good Cheer, the 1.39-1 favorite in 2025; and Pretty Mischievous, a 10.37-1 longshot in 2023.

Here are the historical angles you can use to sort through the 2026 Kentucky Oaks contenders:

Tactic speed is an asset

Since 2005, early (tactical) speed has been advantageous in the Kentucky Oaks. The pace is typically modest (no faster than :46.24 for the opening half-mile and 1:11.25 for three-quarters of a mile), so nine of the last 21 winners (43%) were racing first or second after the opening half-mile. Furthermore, 15 of the last 21 winners (71%) were racing in the top five at that juncture, no more than 3 1/2 lengths off the lead.

Fair Grounds is the best place to prep

Nine of the last 21 Kentucky Oaks winners (43%) competed the Grade 2 Rachel Alexandra Stakes (known as the Silverbulletday Stakes prior to 2011) at Fair Grounds. Eight of the last 21 Kentucky Oaks winners (38%) ran in the Grade 2 Fair Grounds Oaks. All told, 10 of the last 21 Kentucky Oaks winners (48%) raced at least once at Fair Grounds leading up to Oaks day.

Consider longshots for top-three finishes

Longshot Oaks winner Pretty Mischievous (Candice Chavez/Eclipse Sportswire)

Since 2005, six out of 21 Kentucky Oaks winners (28.6%) started at double-digit odds, as did 25 out of 63 top-three finishers (39.7%). Longshots often outperform expectations in the Kentucky Oaks.

Bet on proven graded stakes winners

Horses who have already won at the graded stakes level have prevailed in 18 of the last 21 editions of the Kentucky Oaks (85.7%), including the last 12 winners of the race.

Respect horses starting from posts 10-14

Outside post positions are advantageous in the Kentucky Oaks. Since 2005, 22 out of 77 horses (28.6%) starting from posts 10-14 have recorded top-three finishes in the Oaks, compared with 41 out of 185 horses (22%) starting from posts 1-9.

One or two prep races is an ideal racing schedule

Not counting 2020 (when the Kentucky Oaks was postponed until September due to COVID-19), seven of the last eight editions of the Kentucky Oaks have been won by fillies who competed in only one or two races as a 3-year-old leading up to the Kentucky Oaks.

California fillies have struggled in recent years

While California-based fillies like Rags to Riches, Blind Luck, and Plum Pretty used to win the Kentucky Oaks with regularity, California has been riding a cold streak in recent years, producing only one winner (Abel Tasman) in the last 14 years.

Conclusions

Rachel Alexandra Stakes winner Bella Ballerina (Eclipse Sportswire)

History paints a clear picture: Bella Ballerina is the most likely winner of the 2026 Kentucky Oaks.

As a 2-year-old in 2025, Bella Ballerina went 2-for-2, winning her debut before employing pace-tracking tactics to take the Grade 2 Golden Rod Stakes at Churchill Downs. This year, she’s run twice more, leading almost all the way to win the Grade 2 Fasig-Tipton Rachel Alexandra Stakes before finishing a pace-pressing second in the Grade 2 Fasig-Tipton Fair Grounds Oaks.

Bella Ballerina has tactical speed. She prepped at Fair Grounds. She’s a proven graded stakes winner. She’s run only twice this year. She isn’t based in California. And thanks to her defeat in the Fair Grounds Oaks, she may start as a double-digit longshot in the Kentucky Oaks. If she draws an outside post position, Bella Ballerina won’t have any historical obstacles to overcome and must be ranked as a strong win contender.

Good luck with your handicapping!