Kentucky Oaks History

As might be expected in a race with such a long and storied history, many Kentucky Oaks winners have gone on to become year-end champions and even Hall of Fame inductees. The list includes Silverbulletday, who was the Champion Two-Year-Old Filly in 1998 and Champion Three-Year-Old Filly in 1999, the year she won the Oaks.

In 2007, Rags to Riches won the Kentucky Oaks. Five weeks later, she faced males in the Belmont Stakes (G1) and got into an all-time great stretch duel against an all-time great horse, Curlin. She became the first filly in 102 years, since Tanya in 1905, to win the Belmont.

In 2009 the winner was Rachel Alexandra, who, after her Oaks win, ran in the Preakness Stakes and beat a field of 12 males to become the first filly to win the race in 85 years. She was named Horse of the Year for 2009 over Breeders’ Cup Classic (G1) winning mare Zenyatta.

More recently, Untapable won the Oaks in 2014, and then took on older mares and won the 2014 Breeders’ Cup Distaff, on her way to being named Champion Three-Year-Old Filly for the year. Malathaat, the 2021 Kentucky Oaks winner, not only took champion honors as a 3-year-old but also went on to win the Breeders’ Cup Distaff and take champion older female honors at age four.

kentucky oaks hore racing odds

Kentucky Oaks Racing Tips

Before you put a single dollar down at your racebook of choice, make sure to know the major trends in the race. The best prep races for the Kentucky Oaks are the Fair Grounds Oaks (G2) and the Ashland Stakes (G2).

In recent years, the Fair Grounds Oaks has become an important prep race for the Kentucky Oaks, with winners Untapable (2014) and Believe You Can (2012) both winning at Fair Grounds before shipping in for the Oaks. Equally important is the Ashland Stakes at Keeneland, with Monomoy Girl (2018), Cathryn Sophia (2016), and Lovely Maria (2015) all using the Ashland as the prep for their Kentucky Oaks wins. It is important for handicappers to pay close attention to the results of those events when filling out a betting ticket for the race.

As for how they won, while none of the winners went wire-to-wire in the race, all but Princess of Sylmar were forwardly placed throughout the race and were able to pounce on the pacesetters as they made the turn into the stretch, take the lead and then ease away for the win, so it’s important to consider horses that tend to break quickly from the gate and are able to establish a good stalking position early.

In the last seven years, only one of the Kentucky Oaks winners has been the favorite, Malathaat. Two recent winner have returned double-digit odds: 2019 winner Serengeti Empress was a 13 – 1 longshot, and 2020 winner Shedaresthedevil paid 15 – 1.

Historically, one of the most dominant performances in the Kentucky Oaks came in 2009, when the great Rachel Alexandra took the race by a record 20 1/4, incredibly running just a quarter-second off the race record for 1 1/8 miles despite the fact she wasn’t being pushed by any other horses in the race.

Silverbulletday was another popular winner, who was champion filly in the US in both her two-year-old and three-year-old season, and who also won the 1998 Breeders’ Cup Juvenile Fillies. Her offspring have gone on to produce stars like $664,000 earner Shakin It Up and $506,000 earner Govenor Charlie.

There has only ever been one winner disqualified from the Kentucky Oaks. In 1924, Glide was first under the wire but was judged by the stewards to have caused interference in the stretch drive, and the win was awarded to the second-place finisher, Princess Doreen, who would go on to have a Hall of Fame racing career.


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