Kentucky Oaks Picks & Handicapping
Handicapping methodology and prep race coverage for the first Friday in May.
The Kentucky Oaks is the Friday-before-Derby showcase for three-year-old fillies, a Grade 1 race at Churchill Downs and one of the best betting races of the year. The field is smaller than the Derby's, the market is softer, and the handicapping rewards the same attention to pace, class, and trip that our subscribers get on every stakes race we cover. If you're looking for an edge on Oaks Day, this is how we approach it.
When Is the Kentucky Oaks?
The Kentucky Oaks is run the Friday before the Kentucky Derby, typically the first Friday in May, at Churchill Downs in Louisville, Kentucky. It's a Grade 1 stakes for three-year-old fillies at 1⅛ miles on dirt, with a $1.5 million purse and a maximum field of 14 horses.
The Oaks is often overshadowed by the Derby the next day, but serious bettors know it can be the better card to play. A 14-horse field is more predictable than a 20-horse scrum, the favorite typically gets a fair shot without as much traffic trouble, and the public money still leans Derby-heavy, which leaves value sitting on the Oaks board.
The Road to the Kentucky Oaks
Fillies earn Road to the Kentucky Oaks points through a designated series of prep races run between September and April. The top 14 points earners fill the starting gate, with up to four also-eligibles on standby in case of defections. The prep series includes the Ashland, Fair Grounds Oaks, Fantasy, Santa Anita Oaks, and Gazelle, among others.
See the full prep schedule and current points standings: Kentucky Oaks Prep Races.
How We Handicap the Kentucky Oaks
Same methodology we use on every stakes race. What the E-Z Win® Form weighs on an Oaks-scale field:
- Speed ratings calibrated to Churchill Downs dirt, surface, and condition
- Tiering into T1 through T5 so subscribers see at a glance who's live
- Pace projection: who's on the lead and who's closing, since 1⅛ miles rewards runners who can carry speed but aren't sacrificed to early fractions
- Class relief: stakes-to-stakes figures, so you can tell which fillies have actually run at the level
- Trip notes from their prep races: troubled trips, free runs, gate issues, and wide moves that didn't get punished
The ratings aren't morning-line odds. Some of our top-tier Oaks contenders have been double-digit longshots. The point is to find value in a race that's already under-bet relative to its purse.
Last Year's Oaks
For reference, here's the 2025 Kentucky Oaks. Our top pick Good Cheer won the race.
| Fin | # | Horse | Tier | Our Rank | Win | Plc | Shw |
|---|---|---|---|---|---|---|---|
1st | 11 | GOOD CHEER | T1 | #1 | $4.78 | $21.02 | $11.76 |
2nd | 4 | DREXEL HILL | T3 | #12 | $3.62 | $7.48 | |
3rd | 13 | BLESS THE BROKEN | T1 | #3 | $3.02 | ||
4th | 9 | TENMA | T3 | #13 | |||
5th | 12 | ANNA'S PROMISE | T3 | #9 |
Exotic Payoffs
| Wager | Combo | Payout |
|---|---|---|
$1 Daily Double | 9-11 | $7.61$7.61 |
$2 Exacta | 11-4 | $105.82$105.82 |
50¢ Trifecta | 11-4-13 | $360.17$360.17 |
$1 Superfecta | 11-4-13-9 | $4.8K$4,826.35 |
50¢ Pick 3 | 11-9-11 | $46.83$46.83 |
50¢ Pick 4 | 1-4-7-11-9-8-11 | $76.29$76.29 |
50¢ Pick 5 | 4-1-4-7-11-9-8-11 | $427.95$427.95 |
20¢ Pick 6 Jackpot | 4-4-1-4-7-11-9-8-11 | $401.59$401.59 |
$2 Future Wager | POOL 1 - 15 | $6.78$6.78 |
$2 Future Wager | POOL 1 EXACTA 15 - 10 | $647.78$647.78 |
Why the Oaks Is a Bettor's Race
A few reasons the Oaks often plays cleaner than the Derby:
- 14 horses instead of 20. Traffic trouble is real but not chaotic. Competent horses with clean trips can actually get clean trips.
- 1⅛ miles, not 1¼. Most Oaks contenders have raced at this distance before. Distance isn't the existential question it is in the Derby.
- Softer public betting. Recreational money stays on the Derby card. Oaks pools lean toward serious bettors, which means the form matters more than the narrative.
- Payouts punch above their weight. Longshot Oaks winners aren't uncommon, and the exotic payouts benefit from a field where the public's chalk isn't as concentrated.
If you're playing the Oaks/Derby double or the Oaks Pick 4, the Oaks leg is where disciplined handicapping pays the best.
Get Our Kentucky Oaks E-Z Win® Form
The E-Z Win® Form for the Kentucky Oaks gives you:
- Our full tier rankings for all Oaks runners
- Speed figures calibrated to Churchill Downs dirt
- Detailed past performances and workouts for each horse
- In-depth horse, jockey and trainer stats
- The same format subscribers use on every stakes race all year
See a sample E-Z Win® Form · See pricing
Frequently Asked Questions
When is the next Kentucky Oaks?
The Kentucky Oaks is always the Friday before the Kentucky Derby at Churchill Downs, typically the first Friday in May.
How is the Kentucky Oaks different from the Kentucky Derby?
The Oaks is Grade 1 for three-year-old fillies only, 1⅛ miles, with a 14-horse maximum field and a $1.5 million purse. The Derby is open to colts, fillies, and geldings at 1¼ miles with a 20-horse field and a $5 million purse.
How do fillies qualify for the Kentucky Oaks?
They earn points through a designated series of Road to the Kentucky Oaks prep races. The top points earners fill the 14-horse field, with up to four also-eligibles on standby for defections. Our prep races page tracks the current standings.
What is the Oaks/Derby double?
A daily-double wager that pays off if you pick both the Oaks winner on Friday and the Derby winner on Saturday. It's one of the highest-EV wagers of the year because Oaks outcomes can be non-chalk but the Derby market usually prices the favorite short.
How long is the Kentucky Oaks?
1⅛ miles (9 furlongs). Most Oaks contenders have raced at this distance or close to it before Oaks Day, so distance adaptation isn't the Derby-sized question mark it would be the next day.
Who has the best record handicapping the Kentucky Oaks?
We'll let the results speak. See the 2025 Oaks results - our top pick won.