Handicapping the 2021 Kentucky Oaks

·4 min read
Handicapping the 2021 Kentucky Oaks

While most casual fans anxiously await the Kentucky Derby on Saturday afternoon, Friday’s main event at Churchill Downs should not go overlooked, as three-year-old fillies will be traveling a mile-and-one-eighth in the Grade 1 Kentucky Oaks. From a betting standpoint, the Kentucky Oaks is a race that features a relatively evenly matched group of fillies who do not have nearly as many questions to answer as the boys running on Saturday do, leading to a more enjoyable betting / viewing event (in my opinion). Below you will find the most likely winner of the Kentucky Oaks, a horse who may offer some value in the race, along with a longshot to keep an eye on Friday afternoon.


Ever since she debuted in October of last year, Malathaat (#10, 5/2 morning line odds) has been considered a filly who has immense potential. Based on her perfect 4-for-4 career record to this point, it is safe to say she is well on her way to living up to that promise, and there is no reason to think she is not going to run a giant race on Friday afternoon. Trained by Todd Pletcher, this three-year-old filly has a regal pedigree; her sire, Curlin, was Horse of the Year in 2007, and her dam, Dreaming of Julia, was a multiple graded stakes winner and favorite in the 2013 Kentucky Oaks. Running style wise, Malathaat is not blessed with a great deal of early speed, but that should not hinder her too badly in this spot. The pace looks as though it will be on the swift side, allowing this filly ample time to relax midpack before unleashing her run rounding the far turn. Her morning line odds of 5/2 (roughly 28% chance of victory) seem accurate and would represent fair value.


A filly like Pauline’s Pearl (#1, 20/1 morning line odds) appears to be entering this year’s Oaks headed the right direction, as she has never taken a step backward at any point in her five-race career. Trained by Hall of Famer Steve Asmussen, Pauline’s Pearl’s most recent start in the Fantasy at Oaklawn Park is better than the past performances may suggest, as she was hung three-to-four wide throughout before inching clear in deep stretch. The mile-and-one-eighth distance of Friday’s race should not be an issue for her, and it is not as though she is any slower than the fillies who are likely to be much shorter prices by post time. The 20/1 morning line odds assigned to Pauline’s Pearl do not seem realistic; something closer to 10/1 odds (roughly 9% chance of winning) feel more reasonable, with odds of 8/1 (roughly 11% chance of winning) or higher representing fair value.

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While her form may look on the spotty side, there’s reason to believe Millefeuille (#14, 20/1 morning line odds) is prepared to run the best race of her life in the Kentucky Oaks. Despite only having one victory to her name in five lifetime starts, the Bill Mott trainee has run well in every start – except for her seasonal debut in the Davona Dale at Gulfstream Park on February 27, but she has an excuse for that effort. In the Davona Dale, Millefeuille was prepared to unleash her run when she was stopped in traffic, losing all momentum, and effectively being shut down for the remainder of the race. For all intents and purposes, the Davona Dale was a non-effort, meaning she likely did not get any fitness from the race. Her second start of the year in the Gulfstream Park Oaks can be treated as her first start of the year based on this logic, and she put forth a credible effort. A strong move rounding the far turn put the daughter of Curlin into the lead before she flattened out down the lane, fading to a second-place finish. Millefeuille ran like a “short” horse that day, meaning she likely needed the race from a fitness standpoint and stands every reason to take a step forward in her next start – which will be in Friday’s Oaks. At odds likely north of 15/1, Millefeuille is worth considering in the Kentucky Oaks.


1) 14 – Millefeuille, 20/1 ML
2) 10 – Malathaat, 5/2 ML
3) 1 – Pauline’s Pearl, 20/1 ML
4) 6 – Travel Column, 3/1 ML