The $1.5 million, Grade 1 Kentucky Oaks dates back to 1875 and boasts an impressive roster of winners. The 150th running of the 1 1/8-mile race is slated for May 3 at Churchill Downs, where a deep and talented group of 3-year-old fillies will battle for a historic victory.

Handicappers hoping to select the 2024 Kentucky Oaks winner are advised to review the last 20 years of Kentucky Oaks history before placing their bets. Doing so reveals a number of prominent trends that can help identify the key contenders for victory.

Here are eight such trends to keep in mind when handicapping the Kentucky Oaks:

Favor fillies with early speed

It pays to bring early speed to the Kentucky Oaks. Nine of the last 20 Kentucky Oaks winners were racing in first or second place after the opening half-mile, and 14 of the last 20 winners were racing within 3 1/2 lengths of the early lead.

Genuine deep-closing winners are uncommon in the Kentucky Oaks. Secret Oath rallied from midfield in 2022, but in the last 20 years only Abel Tasman (2017), Princess of Sylmar (2013), Blind Luck (2010), and Lemons Forever (2006) have rallied from at or near the back of the pack to prevail.

One reason might be the typically modest pace of the Kentucky Oaks. A genuinely fast pace unfolded in 2004, but since then the fastest half-mile fraction has been :46.24 and the quickest time for three-quarters of a mile has been 1:11.25 — both modest splits by Grade 1 standards.

Pletcher and Cox are formidable trainers

Hall of Fame trainer Todd Pletcher (Eclipse Sportswire)

Trainers Todd Pletcher and Brad Cox have enjoyed plenty of success in recent renewals of the Kentucky Oaks. Pletcher has recorded four Oaks wins courtesy of Ashado, Rags to Riches, Princess of Sylmar, and Malathaat, while Cox has won twice with Monomoy Girl and Shedaresthedevil.

Even when Pletcher and Cox don’t win the Oaks, they’re apt to have fillies right in the thick of things. Pletcher saddled Oaks runners-up Gambling Girl and Nest in 2023 and 2022, while Cox finished third and fourth with The Alys Look and Wet Paint in 2023.

Fair Grounds is the best place to prep

Fair Grounds in Louisiana has been a key proving ground for future Kentucky Oaks winners. Exactly half of the last 20 Kentucky Oaks winners raced at Fair Grounds during the winter of their 3-year-old season. That includes six fillies since 2012 who competed in the Grade 2 Rachel Alexandra Stakes and eight fillies since 2004 who ran in the Grade 2 Fair Grounds Oaks.

The recent record of the Rachel Alexandra has been particularly impressive: Pretty Mischievous (2023), Serengeti Empress (2019), Monomoy Girl (2018), and Untapable (2014) all managed to win both the Rachel Alexandra and the Kentucky Oaks, while Lovely Marie (2015) and Believe You Can (2012) parlayed Rachel Alexandra defeats into Kentucky Oaks victories.

Horses exiting defeats shouldn’t be underestimated

You might assume fillies entering off flashy victories have the best record of success in the Kentucky Oaks, but truth be told they haven’t held an edge over fillies who lost their final prep race. Over the last 20 years, 10 Kentucky Oaks winners exited victories and 10 came off losing efforts, so a last-out victory isn’t a prerequisite for success in the Kentucky Oaks.

Favorites perform well, but so do double-digit longshots

Shedaresthedevil winning 2020 Kentucky Oaks (Eclipse Sportswire)

Favorites have a fine success rate in the Kentucky Oaks. Since 2004, they’ve gone 7-for-20 (35%), with Ashado, Rags to Riches, Proud Spell, Rachel Alexandra, Blind Luck, Untapable, and Malathaat delivering for favorite backers.

But longshots also perform well in the Kentucky Oaks. In the last dozen years alone, we’ve seen Believe You Can, Princess of Sylmar, Serengeti Empress, Shedaresthedevil, and Pretty Mischievous deliver victories at double-digit odds. Throw in the 47-1 upset of Lemons Forever in 2006, and longshot winners are almost as common as winning favorites.

It’s also worth noting that 23 of the last 60 Kentucky Oaks trifecta finishers (38.3%) started at double-digit odds. Even if you play a favorite on top, looking for live longshots to finish second or third is a sound strategy.

Stakes winners, especially graded stakes winners, have an edge

In searching for live longshots, it’s best to avoid fillies who haven’t enjoyed success against stakes company. The last Kentucky Oaks winner who hadn’t previously won a stakes race was Lemons Forever in 2006, and since then 15 out of 17 Kentucky Oaks winners entered with a graded stakes win on their racing record. If you’re going to bet a longshot, choose one with a stakes win to her credit.

Posts 10 and wider are favorable

Fillies drawn in wide post positions have performed well in the Kentucky Oaks. Since 2004, 20 of the 60 fillies to finish in the Kentucky Oaks trifecta (33%) started from post 10 or wider, including 2023 winner Pretty Mischievous who broke from post 14.

This is a rather remarkable stat considering the Kentucky Oaks doesn’t always draw a full field. On three occasions since 2004, less than 10 fillies started in the Kentucky Oaks, meaning there weren’t any runners breaking from post 10 or wider.

To put it another way, since 2004, 20 out of 70 fillies (29%) starting from posts 10 and wider have finished in the Kentucky Oaks trifecta, compared with 40 out of 176 fillies (23%) breaking from posts 1-9.

Posts 1 and 2 are detrimental

Unsurprisingly given the data point above, post positions 1 and 2 are a bit disadvantageous in the Kentucky Oaks. While Secret Oath and Ashado have managed to win from the rail, they’re the only two fillies in the last 20 years to crack the Kentucky Oaks trifecta from post 1. And during the same timeframe, post 2 has produced only four top-three finishes.

Conclusions

Rising star Tarifa (Lou Hodges, Jr. /Hodges Photography)

Last year, our historical analysis identified Pretty Mischievous as the most likely winner of the 2024 Kentucky Oaks, and bettors who embraced history caught a $22.74 win payoff for a $2 bet when Pretty Mischievous battled her way to victory by a neck.

Pending the post-position draw, history is fairly decisive in sorting through this year’s Oaks contenders. Tarifa, whose 3-for-3 record this season includes victories in the Rachel Alexandra Stakes Presented by Fasig-Tipton and Fair Grounds Oaks Presented by Fasig-Tipton, looks formidable for two-time Kentucky Oaks-winning trainer Brad Cox. She’s shown tactical speed in all three of her starts this year, and so long as she draws an outside post there’s nothing to dislike about Tarifa from a historical standpoint.

Leslie’s Rose is another logical contender. Hailing from the barn of Todd Pletcher, Leslie’s Rose has compiled a 3-for-4 lifetime record highlighted by a three-length victory in the Grade 1 Central Bank Ashland Stakes at Keeneland. She didn’t race at Fair Grounds during the winter, but Leslie’s Rose brings tactical speed to the table and is a pretty solid match for the historical profile of a Kentucky Oaks winner.

What about longshots? Our Pretty Woman has yet to win a stakes, but she finished only three-quarters of a length behind Tarifa when coming home second in the Fair Grounds Oaks. Our Pretty Woman set the pace in the Fair Grounds Oaks, just as she did when wiring a 1 1/16-mile allowance at Fair Grounds two starts back, so we know she has the tactical speed to work out a favorable trip in the Kentucky Oaks.

All told, Our Pretty Woman fits many of the historical trends outlined above. The fact she came within a length of beating Tarifa last time out suggests Our Pretty Woman is a compelling longshot contender for Hall of Fame trainer Steve Asmussen, a two-time winner of the Kentucky Oaks.

Good luck with your handicapping, and enjoy the race!