Kentucky Oaks Race

The Kentucky Oaks is one of the oldest and most prestigious races in the country. Restricted to three-year-old fillies, the race is the female equivalent of the Kentucky Derby, though fillies are also eligible to compete in the Run for the Roses. Traditionally held on the Friday before the Kentucky Derby, Kentucky Oaks Day has grown into a major event of its own right and is one of the most anticipated Thoroughbred horse racing events on the calendar.

The Kentucky Oaks is a Grade 1 level race with a purse of $1.25 million. The race is contested at a mile and an eighth (nine furlongs) on the dirt at Churchill Downs racetrack in Louisville, Kentucky, beneath the iconic Twin Spires. While the winner of the Kentucky Derby gets a blanket of roses, the Kentucky Oaks champion gets a blanket made of lilies.

Kentucky Oaks Betting Online

As one of the most important races of the year for three-year-old fillies, the Kentucky Oaks typically attracts a large and competitive field. Even if you cannot make it to Churchill Downs to watch the Kentucky Oaks in person, you can cash in on the best odds on the Kentucky Oaks through one of these recommended racebooks and not have to miss a bit of the action.

Every one of our recommended racebooks has an excellent user interface, trusted deposit and cash-out functions, and market-leading odds for the Kentucky Oaks, Kentucky Derby, and races all year long. That includes the other Triple Crown races like the Preakness Stakes and Belmont Stakes, the Breeders' Cup races, and even races at your local racetrack day in and day out.

All of these sites also offer betting incentives like sign-up and deposit bonuses, referral benefits, and horse racing rebates for Kentucky Oaks bettors. Take a few minutes now to find out which sites will make you the most money based on what bets you like to make: our expert betting reviews are here to help you find out! Then, you can bet the race with confidence that you are maximizing your profits when you win!

Kentucky Oaks Betting Tips

Handicapping the Kentucky Oaks involves paying close attention to how the Churchill Downs main track is playing in the days leading up to the big race. In addition to watching for hot jockeys, live trainers and any potential track bias, it is worth having an understanding of the history of the Kentucky Oaks as well.

Check The Weather

While Churchill Downs does typically play as a very fair racing surface, the weather can change the dynamic of the race very easily. When rain is in the forecast, the track can be sealed in preparation for the weather and that can make it easier for a front-runner to go gate to wire.

Bird Town, a homebred for Marylou Whitney and trained by Nick Zito, set the stakes record for the mile and an eighth contest in 2003 when she completed the race in 1:48.64 – Untapable came close to meeting that mark in 2014 when she stopped the clock in 1:48.68.

Kentucky Oaks Winners

There have been several fillies in history that have won the Kentucky Oaks and have then gone on to defeat male rivals in a later Triple Crown race. In 2007, Rags to Riches won the Kentucky Oaks and came back to win a stirring stretch duel with Curlin to take the Belmont Stakes.

Rachel Alexandra romped in the Kentucky Oaks in 2009 by a record-setting 20 ¼ lengths, the largest margin of victory in history, and wheeled back only two weeks later to win the Preakness Stakes.

Kentucky Oaks Upsets

There have been some big upsets in Kentucky Oaks history over the years but none moreso than Lemons Forever in 2006. After struggling in her only previous start against stakes company and only having a maiden and allowance/optional claiming victory to her credit, she pulled the upset under jockey Marcus Guidry at odds of 47-1 for trainer Dallas Stewart. It wound up being the lone stakes win of her career.

Jockey Rosie Napravnik made history in 2012 when she piloted the aptly-named Believe You Can to win and became the first female jockey to win the Kentucky Oaks. She came back two years later to repeat that feat with champion Untapable in 2014 before announcing her retirement at the end of that year.

Winningest Kentucky Oaks Jockeys and Trainers

Throughout history, there are two jockeys tied for the most wins with four each – Eddie Arcaro (1951, 1952, 1953 and 1958) and Manuel Ycaza (1959, 1960, 1963 and 1968). However, there are several contemporary jockeys still actively competing and riding for the top barns in the country so those records could be in jeopardy. Jockeys like Florent Geroux, Irad Ortiz, Jr., Mike Smith and John Velazquez are always major contenders on big days in horse racing.

Trainer Woody Stephens is tied for the record for the most victories with five, starting in 1959 and continuing in 1960, 1963, 1978 and 1981. Hot on his heels, however, is veteran trainer D. Wayne Lukas. The Hall of Fame conditioner saddled his first Kentucky Oaks winner in 1982 with Blush With Pride and has since won the race with Lucky Lucky Lucky (1984), Open Mind (1989), Seaside Attraction (1990)...and one more recent horse!

You can never count out The Coach, and Lukas returned in 2022 with Secret Oath, who had dominated the Oaklawn spur of the Kentucky Oaks trail before coming in third behind top male Cyberknife in the Arkansas Derby (G1). Though Nest was favored for Todd Pletcher in the 2022 Kentucky Oaks, Lukas earned his fifth Kentucky Oaks victory when Secret Oath ran her best in Kentucky!

In recent years, trainer Larry Jones has been a dominant force in the Kentucky Oaks with three winners in the past ten years – Proud Spell (2008), Believe You Can (2012) and Lovely Maria (2015). In each of those races, the win was the first for the jockey in the Kentucky Oaks. Proud Spell was ridden by Gabriel Saez, Believe You Can had Rosie Napravnik aboard and the veteran Kerwin Clark was in the irons for Lovely Maria.

Kentucky Oaks Contenders

The likely favorite in the 2023 Kentucky Oaks is Wet Paint, and she comes into the race in very sharp form. Trained by Brad Cox, a two-time Oaks winner already, Wet Paint dominated the Oaks preps at Oaklawn this winter. Oaklawn was where 2022 Kentucky Oaks winner Secret Oath did her prep, meaning that spur of the trail may be rising in importance. She was also able to run excellent races on both wet and dry tracks, meaning that the variance in Louisville's weather will not be a problem for her.

However, when you are betting a race like the Kentucky Oaks with such classy horses and such a full field, it is profitable to look beyond the favorite. Whether you are planning on classic win bets, place bets, or show bets, or you prefer to play exotic wagers like exactas, trifectas, superfectas, or multi-race wagers, finding live mid-priced and even longshot horses is the key to value.

Kentucky Oaks Best Bets

Southlawn has come into her own just in time to be a real force in the 2023 Kentucky Oaks. Though she was no match for stakes company as a two-year-old, her three-year-old season is a different story. She came back a faster and stronger horse after a three-month winter break, tightened up with an allowance win at Fair Grounds, and then romped in the Fair Grounds Oaks (G2) against more experienced stakes horses. Her trainer Norm Casse has a lot of big-race experience as his father Mark's assistant, and he and jockey Reylu Gutierrez tend to slip under the radar.

Affirmative Lady is also coming into the right form into the Kentucky Oaks. Trainer Graham Motion has always figured she had talent: he ran her in Kentucky Oaks points races multiple times as a maiden, and she hit the board in the Demoiselle (G2) and the Busanda. But, she hit her stride in her last two starts, breaking her maiden at Gulfstream and then stepping up to win the Gulfstream Park Oaks (G2) by daylight. She can take her form to different tracks, and she should have the ability to stay the nine-furlong Oaks distance.

Kentucky Oaks bet against

Take a shot against Botanical, who is the second favorite in the Kentucky Oaks future betting. She impressed in the Bourbonette Oaks at Turfway Park, but she has come into her own racing on the synthetic there, and not over conventional dirt like the Oaks is run on. If a horse is a long shot and comes out of the Turfway races, there can be other reasons that the horse is worth betting. But, with a short-priced horse like Botanical, it is better to look elsewhere for runners who are more proven on the surface already.

Kentucky Oaks Current Odds

Odds on the Kentucky Oaks are likely to fluctuate all the way until post time. However, futures are beginning to open at online sportsbooks. Now is the right time to start looking at odds online and see whether you are getting an overlay on your Oaks horse of choice. Remember: betting online is your best bet because you can lock in odds on major races, and do not have to worry about late swings in pari-mutuel odds closer to post time!