2025 Kentucky Oaks prediction, odds, contenders, time: Surprising picks from expert who nailed Breeders’ Cup​on May 2, 2025 at 8:59 pm

Award-winning trainer Brad Cox has won the Kentucky Oaks twice since 2018 and has a shot at making it three in the 2025 Kentucky Oaks on Friday at Churchill Downs. Cox will return to the race with Good Cheer, who is a perfect 6-for-6 in her career. The Kentucky Oaks 2025 will be Good Cheer’s toughest test yet, but the Cox trainee is still the 6-5 betting favorite in the 2025 Kentucky Oaks odds. La Cara (6-1) and Quietside (8-1) round out the top three favorites in the 2025 Kentucky Oaks field, and post time for Friday’s race is 6 p.m. ET. With talented but relatively inexperienced 3-year-olds making for a mind-bending handicapping exercise, you’ll want to see what Santa Anita-based racing reporter and insider Michelle Yu has to say before making any 2025 Kentucky Oaks picks.

Few people in racing are as well-connected as Yu. An on-air host and reporter who has provided racing analysis for TVG, HRTV and the Breeders’ Cup, Yu has spent a lifetime in racing. Prior to her television career, she worked for trainers Steve Asmussen and Ron Moquett. She also is married to Santa Anita-based trainer Ryan Hanson.

Yu also has tremendous handicapping chops. In the last two years, Yu nailed the winners of the Pegasus World Cup, Santa Anita Derby, Apple Blossom Handicap, Met Mile, Breeders’ Cup Classic, Robert B. Lewis Stakes, Saudi Cup, and San Felipe Stakes, among others. She also nailed the race-day result of the Derby in 2021 and 2023. Anyone who has followed her on those picks on betting sites like FanDuel Racing, TwinSpires and 1/ST BET is up huge.

Now, Yu has handicapped the 2025 Kentucky Oaks lineup, made her picks and constructed her best bets. You can head to SportsLine now to see them.

Top 2025 Kentucky Oaks predictions

One surprise: Yu is high on La Cara, even though she’s an underdog at 6-1. La Cara has the advantage of winning at Churchill Downs earlier in her career, taking first under the Twin Spires in the Pocahontas Stakes last September.

She has two first-place finishes in her last three starts, most recently winning the Central Bank Ashland Stakes in April. La Cara is also the daughter of 2007 Derby winner Street Sense. Her mix of pedigree and experience make it easy to see why Yu calls La Cara a “big contender.” You can see all of Yu’s 2025 Kentucky Oaks bets here.

How to make 2025 Kentucky Oaks picks

Yu is also eyeing a double-digit longshot who “hasn’t really been tested” and could turn heads at Churchill Downs. She is including this horse in her 2025 Kentucky Oaks bets, and so should you. She’s sharing which 2025 Kentucky Oaks horses to back at SportsLine.

So who wins the 2025 Kentucky Oaks? And which horse shocks at Churchill Downs on Friday? Visit SportsLine to see Yu’s picks for the Kentucky Oaks 2025, all from the Santa Anita-based racing insider who nailed the Breeders’ Cup Classic, and find out. 

2025 Kentucky Oaks odds, post positions