Kentucky Oaks Betting Guide: Strategies, Statistics & Picks (Derby Week)

2025 Kentucky Oaks Preview

Held at the Churchill Downs racetrack is the Kentucky Oaks, this Group 1 is run in May of each year, it is open to three-year-old fillies only and is run over one mile and one furlong.

Established in 1875, the race is usually run the day before the Kentucky Derby takes place, the winner is presented with a garland of lilies which is also known as the "Lillies for the Fillies".

Kentucky Oaks Picks

Our dedicated Churchill Downs Betting Picks will not only bring you predictions from the OLBG handicappers for the upcoming card that includes the Kentucky Oaks but will also have predictions for each meeting at Churchill Downs throughout the season so be sure to head over there. Whilst we wait for the 2025 Kentucky Oaks remember you can get daily racing predictions from the expert handicappers on the racing predictions page.

Kentucky Oaks Content

• Kentucky Oaks Past Winners
• Kentucky Oaks Trainer Statistics
• Kentucky Oaks Jockey Statistics
• 2025 Kentucky Oaks Trends
• Kentucky Oaks Trend Analysis
• Other Graded races at Churchill Downs Racetrack

Quickest Run Kentucky Oaks Renewals

When looking over the past 10 renewals, a time of 1:48.28 was set by Shedaresthedevil in 2020, which is the quickest time over that period, the runner was trained by Brad H Cox and ridden by Florent Geroux. The slowest winning time was set in 2017 when Abel Tasman won in a time of 1:51.62, booked to ride was Mike E Smith by the trainer Bob Baffert. Below are the top three quickest-run Kentucky Oaks over the last 10 renewals.

1. Shedaresthedevil (1:48.28) in 2020
2. Malathaat (1:48.99) in 2021
3. Monomoy Girl (1:49.13) in 2018

Kentucky Oaks Past Winners

Here are the Kentucky Oaks past winners for the last 10 renewals. Each row details the year of the race, the winning time, and the horse that won along with the cloth number, age, sex, the weight of the horse & which starting gate the horse came from. The trainer of the horse at the time of winning the Kentucky Oaks as well as the jockey is also displayed along with the moneyline odds the horse was sent off.

Where have the winning runners come from?

Here are the countries where the winning trainers of the Kentucky Oaks have been based:

• USA: 10 winners with an additional 19 placings from 129 runners
• CAN: 0 winners with an additional 1 placing from 4 runners
• UAE: 0 winners with an additional 0 placings from 1 runner

Kentucky Oaks Trainer Statistics

The leading trainer in the Kentucky Oaks over the last 10 renewals is Brad H Cox who has won the race 2 times. Those 2 winners came from Monomoy Girl (2018) & Shedaresthedevil (2020). There is one trainer who has not had the best of times in the Kentucky Oaks, Steven Asmussen has sent a total of 10 runners to the race without recording any wins.

Here are some of the most active Kentucky Oaks trainer statistics over the last 10 renewals.

Kentucky Oaks Jockey Statistics

The leading jockey in the Kentucky Oaks over the last 10 renewals is Florent Geroux who has won the race 2 times. Those 2 winners came from Monomoy Girl (2018) & Shedaresthedevil (2020).

Here are some of the most active Kentucky Oaks jockey statistics over the last 10 renewals.

Kentucky Oaks Trend Analysis

How competitive is the Kentucky Oaks market?

When looking at the over-rounds for the last 10 renewals, the most competitive market was in 2024 when the race had an over-round of 122%. The race in 2020 was a race that was most in the bookie's favor with an over-round of 124%, whilst on average over the last 10 renewals of the Kentucky Oaks, the over-round has been 123%, which means the bookie expects to pay out $100 for every $123 which is bet.

Post Positions of the Kentucky Oaks Winners, Places & Shows

Here are the most recent winning draws along with those who placed and showed:

Best Course for a Kentucky Oaks Prep Run?

The course which has produced the most winners of the Kentucky Oaks is Keeneland, there has been a total number of 4 winners of this race who ran at Keeneland last time out.

Worst Performing Stallions in the Kentucky Oaks

These are the stallions whose offspring have not produced a winner of the Kentucky Oaks despite multiple attempts:

• Medaglia dOro (0 Wins from 5 runners)
• Tapit (0 Wins from 5 runners)
• Uncle Mo (0 Wins from 5 runners)

Biggest Priced Winners of the Kentucky Oaks & Performance of Favorites

Looking at the winning odds over the last 10 renewals, the biggest-priced winner was Shedaresthedevil in 2020, winning for Brad H Cox at odds of 151/10 under the guidance of Florent Geroux. Looking at the runners at the head of the market over the last 10 renewals there has been a total of 1 winning favorite in the race. Remember to bookmark the best racing handicappers page so you can get easy access to the best OLBG racing handicappers. All figures and trends above, such as the horse's previous runs are based on the information that is available on the racing post.

Other Graded races at Churchill Downs racetrack

Here are some other notable races at the Churchill Downs racecourse throughout the racing season that you may be interested in.

Races in May (Derby Week)

• Churchill Downs Stakes
• Derby City Distaff Stakes
• Kentucky Derby
• La Troienne Stakes
• Turf Classic Stakes

Races in November

• Clark Stakes

Kentucky Oaks FAQs

Where is the Kentucky Oaks run?

The Kentucky Oaks is run at the Churchill Downs racetrack each year, you can get Churchill Downs racing predictions all season long as well as for Kentucky Oaks.

When is the Kentucky Oaks?

The Kentucky Oaks takes place around May of each year at Churchill Downs.

Who won the Kentucky Oaks?

The 2024 renewal of the Kentucky Oaks was won by the Kenneth McPeek trained Thorpedo Anna who was ridden by Brian Joseph Hernandez Jr in a time of 1:50.83, owned by Brookdale Racing Inc Mark Edwards Et Al it was sent off at an SP of 9/2. You can view all the recent winners in the Kentucky Oaks Past Winners section of the blog.

Who will win the Kentucky Oaks?

On the day of the race, use the trends in this blog and then compare them to the OLBG racing handicappers' predictions for the Kentucky Oaks, you can do this on the Churchill Downs Picks page which not only will have picks for this race but also picks for Churchill Downs throughout the season. You may also be interested in the Horse Racing Picks page where you can get daily horse racing predictions from all of the US courses.

Who is the top trainer in the Kentucky Oaks?

With a total of two winners over the last ten renewals, it is Brad H Cox who holds the claim as the leading trainer in the Kentucky Oaks. To see which other trainers have a good record in the race, head over to the Kentucky Oaks Trainer Statistics section of the blog.

Who is the top jockey in the Kentucky Oaks?

With a total of two winners over the last ten renewals, it is Florent Geroux who holds the claim as the leading jockey in the Kentucky Oaks. To see which other jockeys have a good record in the race, head over to the Kentucky Oaks Jockey Statistics section of the blog.

Do we have trends for the 2025 renewal of the Kentucky Oaks?

The simple answer is Yes! We have a total of fifteen trends for the Kentucky Oaks which can be found under the Kentucky Oaks Trends section.