Kentucky Oaks 2021 Picks

The 2021 Kentucky Oaks will be run on Friday, April 30, 2021. The race drew fourteen of the best three-year-old fillies in the United States to run a mile and an eighth at Churchill Downs. The stakes are high: a $1,250,000 purse, the famous blanket of lilies, and is forever remembered as the best three-year-old filly of the year.

Where to Bet the Kentucky Oaks

Before you decide who to bet in the Kentucky Oaks, it is important to choose the right horse racing sportsbook for betting the Kentucky Oaks online. All of these sportsbooks are easy-to-use, trusted, and offer excellent odds for the Kentucky Oaks and beyond. They also offer great benefits to their players.




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Kentucky Oaks Entries and Odds

The entire field for the 2021 Kentucky Oaks, one major US horse race, 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

That is the list of entrants for the 2021 Kentucky Oaks. Here are the odds on the leading Kentucky Oaks horses in 2021 at the best online sportsbooks:

Kentucky Oaks Winners OddsBovadaBetOnlineBetUS
Search Results+600+325+300
Travel Column+330+300+300
Pass The Champagne+1100+1500+1500
Crazy Beautiful+900+1500+1500

Free Kentucky Oaks Picks

Let’s learn more about the most interesting and bettable horses entered for the 2021 Kentucky Oaks, including some more formful horses and some intriguing longshots.

Kentucky Oaks Handicapping

Malathaat will probably go off favored in the Kentucky Oaks. She is undefeated in four starts for trainer Todd Pletcher. She is versatile enough to work out a good trip and has already won at the 1 1/8-mile distance, though she has to break from the tricky 10 post and she has never actually raced over the Churchill Downs surface.

Search Results will be a short price as well, but there are reasons to be skeptical. She has won all three of her starts, but she is a speed horse in a race with a lot of speed horses. She also drew very far outside, post 12 of 14. She is certain to be an underlay and the smart money bets against Search Results in the Kentucky Oaks.

The real horse to beat in the Kentucky Oaks is Travel Column. She is trained by Brad Cox and ridden by Florent Geroux, who has won two of the last three Oaks. She is versatile enough to carve out a great trip no matter what, and she is already a Grade 2 winner over the love-it-or-hate-it Churchill Downs surface. She also won the Fair Grounds Oaks, one of the best Kentucky Oaks preps year in and year out.

Her most interesting rival is Steve Asmussen trainee Clairiere. Clairiere did beat Travel Column in the Rachel Alexandra Stakes two starts ago, and may once again get a very nice trip rallying into a sharp pace as she did in that race. Clairiere also has a good record at Churchill Downs, with both a maiden win and a graded stakes placing there.

Kentucky Oaks Longshots

Travel Column and Clairiere are very good horses who should run well. But, the way to make the Kentucky Oaks really pay is to go into the exotic pools to play them alongside some price horses. Consider these longshots to turn those exactas, trifectas, and superfectas into day-makers.

Pauline’s Pearl, also trained by two-time Oaks winner Steve Asmussen, is getting good at the right time. Two back she rallied nicely through horses to finish second in the Honeybee at Oaklawn, and then last out she won the Fantasy Stakes there. She is bred well to stretch out to the Oaks distance and the rail has been playing very well at Churchill Downs.

Brad Cox has a very live longshot in Coach. Coach ran two good races at Churchill Downs last year, so she will appreciate returning to the surface. She will be able to rally smartly into the sharp pace in front. And, her jockey Luis Saez just finished up an excellent Keeneland meet and has started Churchill just as hot.

Kentucky Oaks Picks

These are the bets to consider making on the Kentucky Oaks.

  • $10 win on Travel Column
  • $10 exacta box: Travel Column with Clairiere
  • $5 exacta key: Travel Column with Malathaat, Pauline’s Pearl, Coach
  • $5 show on Pauline’s Pearl, Coach
  • $1 trifecta key: Travel Column with Clairiere, Malathaat, Pauline’s Pearl, Coach

Travel Columnto win the Kentucky Derby
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Kentucky Oaks Day Picks

Though the Kentucky Oaks is Friday’s feature at Churchill Downs, the day features a full assortment of rich stakes races featuring the best horses in the country. It includes an all-stakes Pick 6 featuring six rich races in a row.

Here are the horses to make sure to use in the other races on that Pick 6, or to consider betting to win throughout the day:

  • Race 6 – $400,000 Alysheba Stakes: Maxfield, Roadster
  • Race 7 – $300,000 Edgewood Stakes: Aunt Pearl, Gift List
  • Race 8 – $500,000 La Troienne Stakes: Dunbar Road, Paris Lights, Sanenus
  • Race 9 – $300,000 Eight Belles Stakes: Make Mischief, Kalypso, Dayoutoftheoffice
  • Race 10 – $250,000 Twin Spires Turf Sprint: Fast Boat, Diamond Oops, Fiya
Rowan Ward

Rowan has been working in the horse racing industry for nearly two decades, moving up from groom to horse owner, to marketing and media. She learned the tricks of handicapping while working in horse racing broadcasting both in the United States and Canada. In her spare time, she loves to read and take care of the farm animals: sheep, goats, ducks, and chickens.

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