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Wed 28/04/2021 - 03:58 EDT

Kentucky Oaks 2021 Picks

On Friday, April 30, 2021, fourteen of the best three-year-old fillies in the country will complete in the 2021 Kentucky Oaks. The winner gets the best share of a $1,250,000 purse, the iconic blanket of lilies, and a place in horse racing history.

Travel Column is projected to be the 2021 Kentucky Oaks favorite. These are the odds on the top contenders:

Horses bovada gt-bets betonline


+300 TBA +300
Travel Column +375 TBA +425


+600 TBA +800

Search Results

+600 TBA +650

Crazy Beautiful

+800 TBA +800
Pass the Champagne +1200 TBA +1400

Betting the Kentucky Oaks

Though having expert Kentucky Oaks picks are important, it is just as important to know where you can bet the Kentucky Oaks online. You no longer have to go to the track or to an OTB to bet the Kentucky Oaks. Instead, you can get the best odds from the comfort of your home.

Many trusted online sportsbooks are offering excellent bonuses, rebates, and features for everyone betting on the Kentucky Oaks. Make your accounts at these top sportsbooks and be ready to get the best Kentucky Oaks odds!

Kentucky Oaks Predictions

Before handicapping the Kentucky Oaks, it helps to know who the contenders are.

Kentucky Oaks Horses

The field for the 2021 Kentucky Oaks, including post positions, trainers, and jockeys, is as follows: 

  1. Pauline’s Pearl: Steve Asmussen/Ricardo Santana, Jr.

  2. Maracuja: Rob Atras/Kendrick Carmouche
  3. Clairiere: Steve Asmussen/Tyler Gaffalione
  4. Crazy Beautiful: Ken McPeek/Jose Ortiz
  5. Pass the Champagne: George Weaver/Javier Castellano
  6. Travel Column: Brad Cox/Florent Geroux
  7. Ava’s Grace: Robertino Diodoro/David Cohen
  8. Moraz: Michael McCarthy/Flavien Prat
  9. Coach: Brad Cox/Luis Saez
  10. Malathaat: Todd Pletcher/John Velazquez
  11. Will’s Secret: Dallas Stewart/Jon Court
  12. Search Results: Chad Brown/Irad Ortiz, Jr.
  13. Competitive Speed: Javier Gonzalez/Chris Landeros
  14. Millefeuille: William Mott/Joel Rosario

Kentucky Oaks Handicapping

That is the full list of contenders, but let’s check in with the horses who are going to get a lot of betting interest, as well as some of the longshots who will help you make a big profit betting the 2021 Kentucky Oaks.

Malathaat has a good chance of being the Kentucky Oaks favorite. She is undefeated in four starts, including a victory in the Ashland Stakes at Keeneland. She is trained by three-time Kentucky Oaks winner Todd Pletcher, and her jockey John Velazquez won the Oaks with Pletcher once. She is pace versatile and already a winner at the 1 1/8-mile distance, but has to handle a tough post.

Travel Column will be the other horse vying for favoritism. Her trainer Brad Cox and her jockey Florent Geroux have won two of the last three Kentucky Oaks. She comes into the race off of a win in the Fair Grounds Oaks, perennially one of the best Kentucky Oaks prep races. She is already a two-time winner at Churchill, including the Golden Rod last year.

Clairiere has been trading blows with Travel Column for most of her career; Travel Column has beaten her twice, but this Steve Asmussen trainee got the best of her in the Rachel Alexandra. Clairiere has very good form at Churchill, and there is enough speed drawn into the Oaks to give her a good chance to get the right trip.

Search Results is the other horse likely to get a lot of betting action. She is undefeated after three starts, most recently winning the Gazelle at Aqueduct, going the same 1 1/8-mile distance as the Kentucky Oaks. However, she will be forward in a race with a lot of pace, so be careful unless the track appears to be speed-biased.

Pauline’s Pearl is a live longshot for two-time Oaks winner Steve Asmussen. She rallied well through horses to finish second in the Honeybee, her first attempt in stakes company and then won the Fantasy in her next race. She gets Asmussen’s usual “A” jockey Ricardo Santana, Jr., and is another who will appreciate having pace to reel in.

Coach is another long shot to consider. She is trained by Brad Cox, and no one in Kentucky is riding hotter right now than Luis Saez. As a midpack type, she should appreciate having pace to rally into. She is also bred well for the stretch out to the Oaks distance, and she already has two good races at Churchill last year, including a stakes win.

Free Kentucky Oaks Expert Picks

Here are your free Kentucky Oaks expert picks for the 2021 Kentucky Oaks:

  • $30 Win: Travel Column
  • $5 Win/Place/Show: Pauline’s Pearl, Coach
  • $1 Exacta Key: Travel Column with Clairiere, Pauline’s Pearl, Coach
  • $1 Trifecta Key: Travel Column with Clairiere, Malathaat, Pauline’s Pearl, Coach
  • $1 Superfecta Key: Travel Column with Clairiere, Malathaat, Pauline’s Pearl, Coach

Kentucky Derby Undercard Picks

In addition to the Kentucky Oaks itself, the card on Friday, April 30 at Churchill Downs features five other rich undercard stakes races with some of the best horses in America. These are all excellent races to bet.

Churchill Downs is offering an all-stakes Pick 6 on Kentucky Oaks Day. The wager has a $0.20 minimum and requires you to pick the winners in all six stakes races at Churchill Downs. These are horses you should make sure to use when playing your all-stakes Pick 6 on Friday.

  • $400,000 Alysheba Stakes: Maxfield, Roadster
  • $300,000 Edgewood Stakes: Aunt Pearl, Gift List
  • $500,000 La Troienne Stakes: Dunbar Road, Paris Lights, Sanenus
  • $300,000 Eight Belles Stakes: Make Mischief, Kalypso, Dayoutoftheoffice
  • $250,000 Twin Spires Turf Sprint: Fast Boat, Diamond Oops, Fiya