Kentucky Oaks Betting

How to bet, odds and legal betting apps
Horse racing and sports betting

The Kentucky Derby has a well-deserved reputation as one of the premier horse races in the world, but its sister race, the Kentucky Oaks, is not to be overlooked. Held for 3-year-old fillies, the Kentucky Oaks is also run at Churchill Downs. Its distance is a mile and an eighth (nine furlongs), and the event is usually held on the day before the Kentucky Derby.

The two signature races were both postponed several months last year due to the coronavirus pandemic. This year’s Oaks will be run on Friday, Apr. 30, and it will award a purse of $1.25 million to the top finishers and their connections. Instead of roses, which are awarded to the winner of the Kentucky Derby, the winner of the Kentucky Oaks will earn a garland of lilies known as “Lilies for the Fillies.”

There’s plenty to digest when it comes to the Oaks, including its history, where and how to bet on the race, and how to determine whom the contenders for the lilies will be when the field goes to the Churchill Downs starting gate. Let’s take a closer look at the Kentucky Oaks, and some of the latest tips and predictions for the race.

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How to bet on the Kentucky Oaks legally

Churchill Downs has announced plans to open the facility to a capped number of spectators. If those plans are not changed, the Oaks and Derby Day cards are expected to be operating at about 40-50% of normal capacity.

Assuming the plans remain intact, Churchill Downs will have plenty of wagering windows open, and tellers and machines will be ready to take your bets. If you can’t make it to Louisville, though, there are plenty of other ways to put your money down on your favorite 3-year-old filly.

Online wagering, or advance-deposit wagering, is legal in 43 of 50 states. Unless you live in Alaska, Georgia, Hawaii, Mississippi, North Carolina, South Carolina or Utah, you can bet on the Kentucky Oaks through your computer, tablet, or smartphone.

There are many advance-deposit wagering platforms out there competing for your wagering dollars. Some of the most well-known sites are TVG, which also runs a pair of horse racing television networks, and TwinSpires, which is owned by Churchill Downs.

Bet types for Kentucky Oaks

There are many different ways to play the Kentucky Oaks, and with the large field that will be signed on, there are plenty of different directions betting money can go. This means that the odds on the horse and wager you prefer will likely be pretty generous compared to other races with smaller groups of horses and less money in the pools.

If you’re just starting out, or if you only like one horse in the race, your best bets may be win, place or show wagers. Win bets pay out if your horse wins (naturally), place bets pay out if your horse runs first or second, and show bets pay out if your horse runs first, second or third.

Win odds are what are shown on the tote board leading up to a race. If your horse is 4-1, it means you’ll win $4 for every dollar you wager. A successful $2 win bet, for instance, will return $10 (your original $2 bet, plus an $8 profit). Place and show pools are also able to be viewed before the race, so you’ll be able to see how much money is in those pools and how much you could potentially stand to win on those wagers.

If you like multiple horses, bets known as exotics may tickle your fancy as well. Payoffs for exactas (picking the top two finishers), trifectas (picking the top three finishers) and superfectas (picking the top four finishers) can be sizable if longshots run well.

How odds and payouts work

For reference, the 2020 Kentucky Oaks was won by longshot Shedaresthedevil, who went off at odds of 15-1 and paid $32.20 to win. Swiss Skydiver (5-2) and Gamine (3-5) ran second and third, paying out $3.80 and $2.40 to place and show respectively. Because of this outcome, the $2 exacta paid $118.80, the 50-cent trifecta paid $58.40, and the 10-cent superfecta paid $27.93.

Exotic bet types

Exotics tickets can be constructed in many ways. For example, if you like three horses and want to play exactas, you can play an exacta box and buy all combinations of those runners. This would be a total of six bets (for six combinations), and would cost $6 – a dollar per combination.

You can also “key” horses in certain spots on those tickets, which is a popular practice in superfectas that can be played for 10-cent combinations. If you like a horse to win, and think five other horses could run second, third or fourth, you can key your top pick in the first position and use the other runners underneath. This structure produces 60 combinations, and at a 10-cent minimum, you can punch your ticket for just $6.

Finally, like other races at tracks around the world, you can play the Kentucky Oaks as part of “horizontal,” or multi-race, exotics wagers as well. These include doubles (winners of two races in a row), as well as Pick Threes, Pick Fours, Pick Fives and the Pick Six. These sequences can provide plenty of value, especially if you particularly like another horse in a race either immediately before or immediately after the Oaks.

Potential contenders for the Kentucky Oaks

The top 3-year-old fillies begin proving themselves well in advance of the Oaks. There are a number of signature races leading in to the event, and those who perform well earn points for the Kentucky Oaks leaderboard. To date, five of the fillies in contention have earned more than 100 points.

  • Search Results: Trained by Chad C. Brown, this filly has 1st place finishes at the Busher Invitational Stakes and the Grade III Gazelle Stakes on the resume.
  • Travel Column: Brad H. Cox trains this filly which most recently took down 1st place at the Fair Grounds Oaks and came in 2nd at the Rachel Alexandra.
  • Crazy Beautiful: A Kenneth G. McPeek trained filly whose claim to fame is a 1st place finish at the Gulfstream Park Oaks.
  • Pauline’s Pearl: Steven M. Asmussen is the trainer for a filly who finished 1st at the G111 Fantasy Stakes and 2nd at the Honeybee Stakes.
  • Malathaat: From Todd A. Pletcher comes Malathaat, the winner of both Ashland Stakes and Demoiselle Stakes, G1 and G11 races respectively.

While these five fillies look like the top contenders, anything can happen at the Oaks. For confirmation, look no further than last year when 15-1 longshot Shedaresthedevil pulled off a stunner over 3-5 favorite Gamine and the rest of the field.

Future wagering on the Kentucky Oaks

Churchill Downs traditionally offers one round of future wagering on the Kentucky Oaks, where horse players can get early bets down on their top picks for the race. This year’s future wagering took place from Mar. 5 – 7.  When the pool closed up, just four of the possible selections had future odds of less than 10-1.

  • Clairiere 7-2
  • Malathaat 7-1
  • Travel Column 6-1
  • All other 3 year old fillies 5-1

A few of the fillies who have managed to rack up over 100 points on the road to the Oaks didn’t attract overwhelming attention in the futures pool. Search Results closed out at 31-1, Crazy Beautiful finished at 39-1, while the last price for Pauline’s Pearl was 28-1.

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Notable past winners of the Kentucky Oaks

Since its first running in 1875, the Kentucky Oaks has hosted some of the top 3-year-old fillies in training. As a result, its winners’ list is dotted with champions, Hall of Famers, and horses with terrific backstories leading up to their triumphs beneath the twin spires.

The Oaks earned Grade 1 status in 1978, and one year later, the race drew an all-time great. Davona Dale’s march to racing immortality featured a run of eight consecutive stakes victories, and the spree of impressive wins included the 1979 Kentucky Oaks. She won that year’s Eclipse Award for her division, and she was voted into the Hall of Fame in 1985.

In addition to the usual band of celebrities and public figures, the 1991 Kentucky Oaks was graced by a prominent celebrity owner. Earlier in her 3-year-old season, the filly Lite Light was purchased by rap superstar MC Hammer and his family, whose enterprise went by the name Oaktown Stable.

After winning the Santa Anita Oaks and the Fantasy Stakes, Lite Light was sent to Churchill Downs, where she won the Oaks by 10 lengths as the odds-on favorite and prompted legendary announcer Tom Durkin to utter the phrase “you can’t touch this!” on the national broadcast immediately following the race.

More recently, one of the most dominant efforts in Kentucky Oaks history came in 2009, when Rachel Alexandra was heavily favored to take home the lilies. She didn’t just beat her rivals that day. The Hal Wiggins trainee destroyed them, winning by more than 20 lengths, which set a record for the biggest margin of victory in Kentucky Oaks history.

Shortly after that performance, she was privately purchased and transferred to the barn of trainer Steve Asmussen, who campaigned her to Horse of the Year honors that season and ultimately to a spot in racing’s Hall of Fame.

Fittingly, one of the sport’s biggest races regularly attracts some of its most well-known human participants as well. Hall of Fame jockeys Eddie Arcaro and Manny Ycaza won the Oaks four times apiece, while legendary horseman Woody Stephens conditioned five Oaks winners to lead all trainers.

List of Kentucky Oaks Winners

YearHorseTrainerTime
2020ShedaresthedevilFlorent Geroux1:48:28
2019Serengeti EmpressTom Amoss1:50.17
2018Monomoy GirlBrad Cox1:49.13
2017Abel TasmanBob Baffert1:51.62
2016Cathryn SophiaJohn C. Servis1:50.53
2014Lovely MariaJ. Larry Jones1:50.45
2014UntapableSteven M. Asmussen1:48.68
2013Princess of SylmarTodd A. Pletcher1:49.17
2012Believe You CanJ. Larry Jones1:49.50
2011Plum PrettyBob Baffert1:49.50
2010Blind LuckJerry Hollendorfer1:50.70
2009Rachel AlexandraHal R. Wiggins1:48.87
2008Proud SpellJ. Larry Jones1:50.01
2007Rags to RichesTodd A. Pletcher1:49.99
2006Lemons ForeverDallas Stewart1:50.07
2005SummerlySteven M. Asmussen1:50.23
2004AshadoTodd A. Pletcher1:50.81
2003Bird TownNicholas P. Zito1:48.64
2002Farda AmigaPaulo H. Lobo1:50.41
2001FluteRobert J. Frankel1:48.85
2000Secret StatusNeil J. Howard1:50.30
1999SilverbulletdayBob Baffert1:49.92
1998Keeper HillRobert J. Frankel1:52.06
1997Blushing K. D.Sam B. David, Jr.1:50.29
1996Pike Place DancerJerry Hollendorfer1:49.88
1995Gal in a RuckusJohn T. Ward, Jr.1:50.09
1994SardulaBrian A. Mayberry1:51.16
1993DisputeClaude R. McGaughey III1:52.47
1992Luv Me Luv Me NotGlenn S. Wismer1:51.41
1991Lite LightJerry Hollendorfer1:48.80
1990Seaside AttractionD. Wayne Lukas1:52.80
1989Open MindD. Wayne Lukas1:50.60
1988Goodbye HaloCharles E. Whittingham1:50.40
1987BuryyourbeliefLazaro S. Barrera1:50.40
1986Tiffany LassLazaro S. Barrera1:50.60
1985Fran's ValentineJoseph Manzi1:50.00
1984Lucky Lucky LuckyD. Wayne Lukas1:51.80
1983Princess RooneyFrank Gomez1:50.80
1982Blush With PrideD. Wayne Lukas1:50.20
1981Heavenly CauseWoodford C. Stephens1:43.80
1980Bold 'n DeterminedNeil D. Drysdale1:44.80

The road to the Kentucky Oaks

Like the Kentucky Derby, the Kentucky Oaks has a defined series of prep races, which award points of varying values to the top four finishers. These races take place around the country starting in September of each year, and the top 14 runners are assured of making the big race. If a runner is ruled out, the next-highest horse on the leaderboard would earn the right to run.

The first round of prep races includes races when the fillies are 2-year-olds. This is topped by the Breeders’ Cup Juvenile Fillies, and also includes prestigious races like the Chandelier, Alcibiades and Frizette stakes. In February, the fillies shift to races in the Road to the Oaks Championship Series.

This part of the journey to the event includes races bestowing up to 100 points to each winner, including the Ashland, the Santa Anita Oaks, and the Fantasy.

Kentucky Oaks FAQ

When is the Kentucky Oaks?

The Kentucky Oaks usually takes place on the first Friday in May. However, due to the coronavirus pandemic, the 2020 renewal was postponed to the first Friday in September.

How many horses run in the Kentucky Oaks?

The Kentucky Oaks runs with a field of 14 3-year-old fillies.

What is the winner’s purse in the Kentucky Oaks?

The connections of the winning horse receive $750,000 and a garland of lilies.

How much are Kentucky Oaks tickets?

Various different types of seating are on sale, but note that Churchill Downs will limit ticket sales for this year’s event due to the coronavirus pandemic.

How long does the Kentucky Oaks last?

The Kentucky Oaks has been run at a mile and an eighth every year since 1982, when it was lengthened from its prior distance of a mile and a sixteenth. It usually lasts about one minute, 50 seconds.

Who was the fastest horse to win the Kentucky Oaks?

The stakes record of 1:48.64 was set by Bird Town, who won the Oaks in 2003. That record was threatened by Untapable, when she stopped the timer in 1:48.68 in winning the 2014 renewal.

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