The Kentucky Derby Presented by Woodford Reserve isn’t the only major horse race taking place at Churchill Downs this spring. One day prior to the fabled first Saturday in May, a deep field of three-year-old fillies will race 1 1/8 miles in the $1.25 million Grade 1 Longines Kentucky Oaks.

Just like the Derby, the Oaks has been held every year since 1875. Its long and rich roster of winners is dotted with important names, including recent champions Rachel Alexandra, Blind Luck, Untapable, Abel Tasman, Monomoy Girl, and Malathaat.

The Kentucky Oaks typically draws a large field of talented fillies from around the country, and handicapping the race isn’t always easy. The good news is, examining the recent history of the Kentucky Oaks reveals a number of trends to help identify the most likely winner. Here are eight to keep in mind as the big race approaches:

Speed horses have an advantage

Positional speed is typically an important weapon in the Kentucky Oaks. No fewer than 11 of the last 15 Oaks winners were racing within 3 ½ lengths of the lead after the opening half-mile, including seven fillies who were racing in first or second place.

This can be attributed at least in part to the typically modest pace of the Kentucky Oaks. Unlike the Kentucky Derby, which often features quick fractions, the Kentucky Oaks tends to unfold in relaxed fashion. Over the last 15 years the fastest half-mile fraction has been :46.24, while the quickest time for three-quarters of a mile has been 1:11.25—both modest splits by Grade 1 standards.

Occasionally, late runners do win the Kentucky Oaks. Abel Tasman (2017) closed from far behind to win over a sloppy track, while Princess of Sylmar (2013) and Blind Luck (2010) unleashed similarly big rallies over dry footing. But considering all three won a minimum of four Grade 1 races during their decorated careers, it’s safe to say it takes an elite filly to win the Kentucky Oaks in late-running style.

Respect fillies trained by Todd Pletcher and Brad Cox

Two of the most successful trainers in recent editions of the Kentucky Oaks have been Todd Pletcher and Brad Cox. Pletcher has won the race three times in the last two decades with Ashado (2004), Rags to Riches (2007), and Princess of Sylmar (2013), while Cox has picked up victories courtesy of Monomoy Girl (2018) and Shedaresthedevil (2020).

In short, Pletcher and Cox have accounted for a combined 26% of Kentucky Oaks winners since 2004, so they warrant respect whenever they send a filly to Churchill Downs.

Look for fillies who contested the Rachel Alexandra Stakes

In recent years, one race has exceeded all others as the most productive steppingstone toward the Kentucky Oaks. Since 2012, the 1 1/16-mile Grade 2 Rachel Alexandra Stakes presented by Fasig-Tipton at Fair Grounds has produced five Kentucky Oaks winners. Serengeti Empress (2019), Monomoy Girl (2018), and Untapable (2014) all managed to win both races, while Lovely Maria (2015) and Believe You Can (2012) parlayed defeats in the Rachel Alexandra into victories at Churchill Downs.

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The Grade 2 Fair Grounds Oaks presented by Fasig-Tipton has also been an important prep race, producing half a dozen Kentucky Oaks winners since 2005. All told, seven of the last 15 Kentucky Oaks winners ran at Fair Grounds during the winter of their 3-year-old seasons, establishing the New Orleans oval as a key proving ground for top Kentucky Oaks contenders.

A recent victory isn’t critical

While plenty of Kentucky Oaks winners have arrived at Churchill Downs off impressive victories, it’s just as common for the eventual winner to suffer a defeat in her final prep race. Exactly half of the last 20 Kentucky Oaks winners entered the race off a defeat, demonstrating that a last-out victory isn’t critical for success at Churchill Downs.

Longshots often outrun expectations

Winning favorites aren’t uncommon in the Kentucky Oaks: the last 15 years have seen five favorites (Proud Spell, Rachel Alexandra, Blind Luck, Untapable, and Malathaat) visit the winner’s circle.

But longshots also have a strong record of success. Since 2012, four winners (Believe You Can, Princess of Sylmar, Serengeti Empress, and Shedaresthedevil) started at double-digit odds, so longshot winners are almost as common as winning favorites. In addition, 16 of the last 45 Kentucky Oaks trifecta finishers (36%) started at double-digit odds, so looking for live longshots is important if you want to cash exotic wagers like the exacta and trifecta.

Favor established stakes winners, especially graded winners

Notwithstanding the above stat about longshots, unproven fillies rarely prevail in the Kentucky Oaks. You have to go back to Lemons Forever in 2006 to find a Kentucky Oaks winner who hadn’t previously won a stakes race. Even more remarkable, 14 of the last 16 Kentucky Oaks winners had secured a graded stakes win prior to their success at Churchill Downs.

Upgrade fillies drawn in outside posts

Wide post positions have been anything but detrimental in the Kentucky Oaks. Since 2008, 15 of the 45 fillies to finish in the Kentucky Oaks trifecta (33%) started from post 10 or wider, a remarkable achievement since the race doesn’t always draw a full field. In 2009 and 2020, less than 10 fillies started in the Kentucky Oaks, so there weren’t any runners breaking from post 10 or wider.

Downgrade fillies breaking from posts 1 and 2

On the opposite end of the spectrum, fillies drawn in posts 1 and 2 have been disadvantaged in recent renewals of the Kentucky Oaks. When Secret Oath won from the rail in 2022, she was the first post 1 starter since 2004 to crack the Kentucky Oaks trifecta. And during the same timeframe, post 2 has produced only one top-three finish.

Pretty Mischievous. (Hodges photography)

Conclusions

The field for the 2023 Kentucky Oaks has yet to be finalized. Among the prospective starters, there aren’t any fillies who perfectly match the historical profile of a typical Kentucky Oaks winner. But one of them – Pretty Mischievous – comes pretty close.

Pretty Mischievous is a proven graded stakes winner, having battled to victory in the Rachel Alexandra Stakes presented by Fasig-Tipton at Fair Grounds during the winter. She followed up with a respectable runner-up finish in the Fair Grounds Oaks presented by Fasig-Tipton, so she’s exiting two of the most historically important Kentucky Oaks prep races.

Pretty Mischievous has enough tactical speed to secure a forward position in the Kentucky Oaks, just like Proud Spell, Rachel Alexandra, Plum Pretty, Believe You Can, Monomoy Girl, and Shedaresthedevil. And she seems certain to start at double-digit odds, just like Believe You Can, Princess of Sylmar, Serengeti Empress, and Shedaresthedevil. The fact she enters off a defeat isn’t an issue, and for good measure she’s won twice at Churchill Downs in the past.

You won’t find too many handicappers touting Pretty Mischievous as the most likely winner of the 2023 Kentucky Oaks, but history suggests she’s a strong candidate to outrun expectations and snatch first prize.

Good luck with your handicapping, and enjoy the race!