Kentucky Oaks Betting

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Shedaresthedevil wins the Kentucky Oaks!

The Kentucky Oaks is one of the most eagerly anticipated horse races of the year. It takes place the day before the biggest day in the horse racing calendar in the United States, the Kentucky Derby. The Kentucky Oaks is an exciting event that carries a lot of prestige for the winner. This Kentucky Oaks betting guide looks at the ins and outs of this famous race.

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Our top choice for Kentucky Oaks Betting is TVG. Read our TVG Review to find out why we recommend this operator. The lineup of the Kentucky Oaks horses hasn’t been announced yet, but will be soon after the last race of the Road to the Kentucky Oaks.

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The History of Kentucky Oaks

The Kentucky Oaks is the oldest horse race that is still taking place in the United States along with the Kentucky Derby. In fact, these two races are the longest-running sporting events in the country’s history.

The first-ever Kentucky Oaks took place in May 1875. It was at a time when the Churchill Downs had the name of the Louisville Jockey Club. In addition to the Kentucky Derby, Meriwether Lewis Clark Jr. was the founder of the Kentucky Oaks.

The idea for the Kentucky Oaks came from the British Epsom Oaks that has taken place in Epsom Downs in Surrey, England since 1779. The first-ever winner of the Kentucky Oaks was Vinaigrette, with the top prize being $1,175. The Kentucky Oaks has taken place continually every single year ever since.

It always gets massive attendance numbers, being one of the most popular races in the United States horse racing calendar each year. Since the Kentucky Oaks in 2001, there have been in the region of 100,000 people attending this race every single year. This showcases the increasing popularity of the race, as it was only attracting about half of that number back in the early 1980s.

Normally, the Kentucky Oaks attendance is the third-highest for horse racing each season in the nation. It is usually only behind the Kentucky Derby and the Preakness Stakes in terms of the most attended races.
The Kentucky Oaks is also part of a prestigious set of horse races that makes up the Triple Crown of Thoroughbred Racing. This is along with the Acorn Stakes and the Black-Eyed Susan Stakes.

kentucky oaks trophy
Calvin Borrel with The Kentucky Oaks Trophy. Craiglduncan at English Wikipedia [CC BY-SA]

Happy Visitors for the Kentucky Oaks

As mentioned, attendance numbers for the Kentucky Oaks usually reach the 100,000 mark. This sees a lot of local residents and those from out of state and even out of country coming to attend the Kentucky Oaks each year.

A lot of the local residents go to the infield of the racetrack to enjoy the festival-type atmosphere. There is usually a variety of music acts, games, and vendors for food and drinks that are located around the track

While you cannot legally bring in alcohol with you when attending the Kentucky Oaks, a lot of people try to get creative in order to get around these rules. Naturally, the prices for alcohol and other beverages are going to be higher at the Kentucky Oaks than you could get in a retail store.
A lot of the businesses and schools in the region almost treat the Kentucky Oaks as a form of a holiday. A lot of the schools categorize the day off for the Kentucky Oaks as being an “administrative day”.

The Format of the Kentucky Oaks

The Kentucky Oaks naturally is a Grade I race. There are 14 horses that line up at the starting post each year. It only includes thoroughbred fillies that are three years old. It takes place at the Churchill Downs racetrack each year, which is in Louisville, Kentucky.

The Kentucky Oaks takes place over 1.12 miles. The weight that is universally carried by each of the horse taking part is 121 pounds. This race takes place on Friday, the day before the Kentucky Derby takes place.

For the winner, the top prize in recent years has been set at $750,000. In total, the purse in total is around the $1,250,000 mark. Another part of the prize is the awarding of a massive lilies garland known as the “Lilies for the Fillies”. In addition to the money and the lilies, the winner will also be given a silver Kentucky Oaks trophy.

Kentucky Oaks Records

There are some notable records for those that have partaken in the Kentucky Oaks over the years. The current record time for the Kentucky Oaks at its current distance was achieved in 2003 when Bird Town finished the race in just 1:48:64.

The largest-ever winning margin came in 2009 by Rachel Alexandra who won by 20.25 lengths. The biggest price of a Kentucky Oaks picks winner was in 2006 when at 47/1 Lemons Forever took the top prize at the Kentucky Oaks.

Two jockeys have successfully won the Kentucky Oaks on four occasions, being Eddie Arcaro and Manuel Ycaza. Only one female jockey has won the Kentucky Oaks. This was Rosie Napravnik and she won the race in both 2012 and 2014. Woody Stephens holds the record for the most Kentucky Oaks wins as a trainer, having done so on five occasions. Calumet Farm holds the record for the most Kentucky Oaks wins as an owner, with a total of six titles.

How to Qualify for the Kentucky Oaks

There is a series of qualification events that will allow horses to gain entry into the Kentucky Oaks. This is usually called “Road to the Kentucky Oaks”. These days, this qualification system is based on points, with fourteen horses getting the invite to participate in this legendary race.

There are usually four other horses that are waiting on standby for the race in case one or more of the Kentucky Oaks qualifiers have to pull out for whatever reason. There are 30 different races that make up the qualification period for the Kentucky Oaks. These events stater in September and finish in April the following year, with the Kentucky Oaks usually taking place at the start of May. This year, the Kentucky Oaks has been postponed to September 4.

Horses need to finish a qualifying event in the top four places in order to gain points that contribute to their Kentucky Oaks rankings. The events that carry the most points are those that take place closer to the Kentucky Oaks, usually in March and April. If there is a tiebreaker in terms of the total number of points two or more horses have accumulated, a tiebreaker will be decided by the horse’s total earnings throughout the qualification series.

Kentucky Oaks Betting

There are numerous different Kentucky Oaks betting markets on offer for those looking to place a wager on the race. Naturally, you will likely get better odds the further away from the start of the race that you place your bets.

In the hours leading up to the race, there will be a massive volume of betting, which will drive down the Kentucky Oaks odds for the leading horses

Generally, the field is finalized on Tuesday before the race takes place. This allows you to do your research in advance of the finalized entry list, basing your research on those horses at the top of the qualification rankings.
This allows you to determine your Kentucky Oaks picks. Once the field is finalized, you can complete any further analysis that is needed.

As well as having the popular ‘Win’ and ‘Place’ bets, there are more exotic markets also on offer for Kentucky Oaks betting. You can bet on the order of the top few places in the race, find handicap markets, winning distance and so on.

You are spoilt for choice with the range of markets on offer for Kentucky Oaks betting. Depending on your state, you may have access to legal online horse betting for KY Oaks and Kentucky Derby betting.

Kentucky Oaks Winners

The 2020 winner was Shedaresthedevil, trained by Brad H. Cox and jockeyed by Florent Geroux.

In 2019, the winner of the KY Oaks was Serengeti Empress, watched by 105,000 people at the track. Bettors did not really favor the winner on the day of the race, with its morning KY Oaks odds being 8/1 before drifting out to 13/1 right before the beginning of the race.

It was an impressive victory considering that the owners of Serengeti Express were considering withdrawing the horse from the race earlier in the week due to concerns about bleeding that was occurring in the previous few weeks. However, at the start of the week, the horse turned a corner and recovered nicely to claim the title in the end.

Past Five Winners

The following are the past 5 winners.

2020ShedaresthedevilFlorent GerouxBrad H. CoxFlurry Racing Stables LLC  –  Qatar Racing Ltd.
2019Serengeti EmpressJose OrtizTom AmossJoel Politi
2018Monomoy GirlFlorent GerouxBrad H. CoxDubb/Monomoy/Elkstone/Bethlehem
2017Abel TasmanMike E. SmithBob BaffertChina Horse Club
2016Cathryn SophiaJavier CastellanoJohn Servis     Cash Is King Stable


As you can see, there is a massive amount of history and prestige attached to the Kentucky Oaks. It is a very tough race to get into, with a lot of trainers revolving their annual schedule around gaining entry into the KY Oaks. 

The popularity of the race doesn’t look like slowing down any time soon and there are constantly more Kentucky Oaks betting markets being added with each renewal.