Kentucky Oaks Betting Guide

There isn’t a bigger race of the season for three-year-old fillies than the Grade 1 Kentucky Oaks. The race will take place on the Friday of the Kentucky Derby weekend, and there promises to be a thrilling race once again this year.

Kentucky Oaks Event Details

The Kentucky Oaks is the featured race on the Friday of the Kentucky Derby weekend. The race is open to the most talented three-year-old fillies and is competed over a distance of 1 1/8 miles at Churchill Downs.

It is a hugely lucrative race with a prize fund of $1 million available for the race. The winning connections will get around $750,000 of the prize fund, and it has been a prominent race on the US schedule since 1875.

Kentucky Oaks Race Predictions/Preview

The Kentucky Oaks is always one of the most competitive races of the season, and that looks set to be the case once again in 2021. You can find some of the leading contenders that are expected to line up for the big Grade 1 race below:

  • Search Results

  • Travel Column

  • Crazy Beautiful

  • Pauline’s Pearl

  • Malathaat

  • Soothsay

  • Clairiere

  • Beautiful Gift

  • Will’s Secret

The leading contender in the field, according to the latest betting odds for the Kentucky Oaks, is Travel Column. Brad Cox trains this three-year-old, and she has won three from five career starts. Her most appealing win to date came on March 20th, as she won by two and three-quarter lengths in the Grade 2 Fair Ground Oaks. Clairiere finished back in second in that race, but the Steven Asmussen-trained horse has already beaten Travel Column this season. She held on to win the Grade 2 Rachel Alexandra Stakes at Fair Grounds on February 12th.

Malathaat has been the biggest market mover over the past couple of weeks, as she returned to the track with a fantastic display in the Grade 1 Central Bank Ashland Stakes. The Todd Pletcher-trained horse won by a head from Pass The Champagne. She has now accumulated 110 points on the Kentucky Oaks leaderboard, which sees her sit in fifth place.

Search Results has accumulated the most points to date, as she recently won the Grade 2 Gazelle at Aqueduct. The Chad Brown-trained horse is three from three on the track and can be found at around 7/1 with many of the leading sportsbooks.

Crazy Beautiful is another that has attracted late support in the market for trainer Kenneth McPeek. After winning just twice on five starts in 2020, she has won once from two in 2021. Her most recent win came in the form of the Grade 2 Gulfstream Park Oaks on March 27th.

Pauline’s Pearl is just behind Crazy Beautiful on the leaderboard, as she has accumulated 120 points so far this season. Only Travel Column has accumulated more in non-restricted stakes earnings so far this season. Her 2021 form has been exceptional to this point for trainer Steven Asmussen, as she has won two from three. She most recently won the Grade 3 Fantasy Stakes at Oaklawn Park.

The only defeat that she has suffered this season came as she finished three-quarters of a length behind Will’s Secret in the Grade 3 Honeybee Stakes. However, Will’s Secret recently finished five and a half lengths behind Malathaat at Keeneland in the prior mentioned Central Bank Ashland Stakes.

Kentucky Oaks Event Information/History

The Kentucky Oaks was first run back in 1875. At that time, Churchill Downs was known by its previous name of Louisville Jockey Club. Along with the Kentucky Derby itself, the Oaks is the oldest annual sporting event in the United States and was modeled on the historic Epsom Oaks, which has taken place in the United Kingdom since 1779. The race has been run over its current distance since 1982, with previous renewals taking place over 1 1/16 miles and 1 ½ miles.

Last year’s winner, Shedaresthedevil, holds the record for the quickest Kentucky Oaks win, as she completed the race last year in 1:48.28. However, Rachel Alexandra’s win in 2009 was the widest winning margin, as she won by a staggering 20 and a quarter lengths. Lemons Forever was the biggest priced winner of the Kentucky Oaks, as she won at odds of +4700.

Eddie Arcaro and Manuel Ycaza have both rode winners on four occasions apiece. Meanwhile, Rose Napravnik is the only female jockey to win the race, as she won for the second time in 2014. The race in 2021 will be exclusively live on NBCSN, with a live stream of the race found on

Kentucky Oaks Betting Information

The Kentucky Oaks is one of the biggest betting days of the year in America, which means that there will be a number of different markets available to customers looking to wager their money on the big race.


  • Win: Betting money on the winner of the Kentucky Oaks will be the most popular bet available to customers.

  • Place: Customers will also be able to place a wager on a horse to finish in a place position.

  • Exacta: One of the most difficult markets to get a winner on is the Exacta. Customers must correctly predict the first two horses to finish the race in the correct order.