You know how punters get lost in too much data or bet blindly? I break down the stats and trends so you can feel confident you’re betting with more than just gut instinct.
2027 Kentucky Oaks Preview
The Kentucky Oaks is held each May at the Churchill Downs Racecourse. The Grade 1 is open to three-year-old fillies only and is run over one mile and one furlong.
The race was established in 1875 and 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 Information:
We also have a dedicated Churchill Downs tips page that will cover this race, as well as all the other races on the day. See which runners the OLBG racing tipsters are predicting to win this race and the others on the cards.
Best Horse Racing Betting Sites 2026
How competitive is the Kentucky Oaks market? When looking at the over-rounds for the last 20 renewals, the most competitive market was in 2007, when the race had an over-round of 120%. The race in 2020 was a race that was most in the bookie's favour with an over-round of 124%, whilst on average over the last 20 renewals of the Kentucky Oaks, the over-round has been 122%, which means the bookie expects to pay out £100 for every £122 which is bet.
Below you will find the 2027 Kentucky Oaks Trends. See which patterns have occurred over the recent renewals that you may be able to use for the next renewal. We also have a section that looks at the Kentucky Oaks Trend Analysis.
These are the top three quickest-run Kentucky Oaks races over the last 20 renewals:
- Shedaresthedevil (1:48.28) in 2020
- Untapable (1:48.68) in 2014
- Always A Runner (1:48.82) in 2026
Looking at the future form, is the winner worth following next time out? Over the past 20 renewals, if you had followed the winner of the Kentucky Oaks next time out, then you would have backed a total of 8 winners. Backing all 19 runners who have been out since their win at SP next time out would have returned an LSP of +2.68. Ahead of the 2027 Kentucky Oaks, why not head over to the racing predictions for tips on other races today?
Over the last 20 renewals, it was Shedaresthedevil, trained by Brad H Cox and ridden by Florent Geroux, who set the fastest winning time in the Kentucky Oaks. That runner won the race in a time of 1:48.28 in 2020. At the other end of the scale, it was the combination of trainer Bob Baffert and jockey Mike E Smith with Abel Tasman who set the slowest winning time; the race-winning time was 1:51.62 in the 2017 renewal.
What the expert says...
Andy Powell - Horse Racing Betting Expert - OLBG.com
Kentucky Oaks Past Winners
Here are the Kentucky Oaks past winners for the last 10 renewals. Each row details the race year, the winning horse, and the horse's age & weight. Also detailed is the stall from which the horse came and the total number of runners in the race. The horse's trainer and the jockey at the time of winning the Kentucky Oaks are also displayed, along with the starting price at which the horse was sent off.
| Year | Horse (Drawn) | Info |
|---|---|---|
| 2026 1:48.82 | Always A Runner (USA) 3yo 8-9 (7 of 13) 11/2 | Jose L Ortiz Chad C Brown (USA) |
| 2025 1:50.15 | Good Cheer (USA) 3yo 8-9 (10 of 13) 7/5F | Luis Saez Brad H Cox (USA) |
| 2024 1:50.83 | Thorpedo Anna (USA) 3yo 8-9 (4 of 14) 9/2 | Brian Joseph Hernandez Jr Kenneth McPeek (USA) |
| 2023 1:49.77 | Pretty Mischievous (USA) 3yo 8-9 (14 of 14) 104/10 | Tyler Gaffalione Brendan P Walsh (USA) |
| 2022 1:49.44 | Secret Oath (USA) 3yo 8-9 (1 of 14) 22/5 | Luis Saez D Wayne Lukas (USA) |
| 2021 1:48.99 | Malathaat (USA) 3yo 8-9 (9 of 13) 5/2F | John R Velazquez Todd Pletcher (USA) |
| 2020 1:48.28 | Shedaresthedevil (USA) 3yo 8-9 (7 of 9) 151/10 | Florent Geroux Brad H Cox (USA) |
| 2019 1:50.17 | Serengeti Empress (USA) 3yo 8-9 (13 of 14) 13/1 | Jose L Ortiz Thomas Amoss (USA) |
| 2018 1:49.13 | Monomoy Girl (USA) 3yo 8-9 (14 of 14) 13/5 | Florent Geroux Brad H Cox (USA) |
| 2017 1:51.62 | Abel Tasman (USA) 3yo 8-9 (13 of 14) 92/10 | Mike E Smith Bob Baffert (USA) |
Where have the winning runners come from?
Here are the countries where the winning trainers of the Kentucky Oaks have been based:
- USA: 20 winners with an additional 37 placings from 244 runners
- CAN: 0 winners with an additional 2 placings from 9 runners
- UAE: 0 winners with an additional 0 placings from 1 runner
2026 Kentucky Oaks Replay
Kentucky Oaks Trainer Statistics
There are multiple leading trainers in the Kentucky Oaks over the last 20 renewals, with Todd Pletcher, Brad H Cox, and J Larry Jones having all won the race three times. Todd Pletcher winners have been with Rags To Riches (2007), Princess Of Sylmar (2013) and Malathaat (2021). Brad H Cox winners have been with Monomoy Girl (2018), Shedaresthedevil (2020) and Good Cheer (2025). J Larry Jones winners have been with Proud Spell (2008), Believe You Can (2012) and Lovely Maria (2015). The only other trainer to have recorded multiple wins in the Kentucky Oaks is Bob Baffert (2 wins).
Here are some of the top Kentucky Oaks trainer statistics over the last 20 renewals (R = Runners, W = Winners, P = Places including winners, Win LSP is based on 1pt Win and EW LSP is based on 0.5pt Win & 0.5pt Place):
| Trainer | R-W-P | Win | EW |
|---|---|---|---|
| Todd Pletcher | 23-3-9 | +23.00 | +12.39 |
| Brad H Cox | 14-3-4 | +8.10 | +3.96 |
| J Larry Jones | 6-3-4 | +20.50 | +12.16 |
| Bob Baffert | 13-2-3 | +4.50 | -1.13 |
| Kenneth McPeek | 14-1-3 | -8.50 | -7.78 |
| Steven Asmussen | 11-1-3 | -9.00 | -4.62 |
| D Wayne Lukas | 8-1-3 | -2.60 | +0.70 |
| Chad C Brown | 6-1-4 | +0.50 | +3.87 |
| Thomas Amoss | 4-1-1 | +10.00 | +4.80 |
| Brendan P Walsh | 2-1-1 | +9.40 | +5.24 |
Kentucky Oaks Jockey Statistics
There are multiple leading jockeys in the Kentucky Oaks over the last 20 renewals, with Mike E Smith, Luis Saez, Florent Geroux, Jose L Ortiz, and Rosie Napravnik having all won the race twice. Mike E Smith winners have been with Princess Of Sylmar (2013) and Abel Tasman (2017). Luis Saez's winners have been with Secret Oath (2022) and Good Cheer (2025). Florent Geroux winners have been with Monomoy Girl (2018) and Shedaresthedevil (2020). Jose L Ortiz winners have been with Serengeti Empress (2019) and Always A Runner (2026). Rosie Napravnik's winners have been with Believe You Can (2012) and Untapable (2014). Multiple jockeys have not had the best of times over the last 20 renewals in the Kentucky Oaks; Joel Rosario (0-12), Julien R Leparoux (0-11) and Irad Ortiz Jr (0-10) have all failed to produce a single winner despite having multiple rides in the race.
Here are some of the top Kentucky Oaks jockey statistics over the last 20 renewals (R = Runners, W = Winners, P = Places including winners, Win LSP is based on 1pt Win and EW LSP is based on 0.5pt Win & 0.5pt Place):
| Jockey | R-W-P | Win | EW |
|---|---|---|---|
| Mike E Smith | 10-2-3 | +40.20 | +21.65 |
| Luis Saez | 10-2-2 | -2.20 | -4.52 |
| Florent Geroux | 9-2-3 | +10.70 | +4.68 |
| Jose L Ortiz | 8-2-4 | +12.50 | +12.80 |
| Rosie Napravnik | 4-2-3 | +12.80 | +8.98 |
| John R Velazquez | 14-1-6 | -10.50 | -4.39 |
| Javier Castellano | 13-1-5 | -7.30 | -2.93 |
| Brian Joseph Hernandez Jr | 8-1-1 | -2.50 | -4.30 |
| Rafael Bejarano | 8-1-1 | -5.70 | -6.22 |
| Calvin H Borel | 6-1-2 | -4.70 | -3.38 |
2027 Kentucky Oaks Trends
Favourites finishing positions (oldest to latest): 1, 1, 1, 1, 4, 3, 4, 1, 4, 6, 11, 3, 5, 3, 1, 2, 4, 2, 1, 6
The percentage shown is the proportion of runners who fell under that factor. High percentages are less appealing than lower ones, as you would expect them to do well. The trend information is based on the available information on the Racing Post in terms of previous runs, etc.
- 20 / 20 (59%) - No bigger than 47/10 (LTO)
- 20 / 20 (60%) - Achieved an RPR of 104+ (Season)
- 20 / 20 (64%) - Break of 26 - 145 days (Last Win)
- 20 / 20 (65%) - Carried 118 - 123lbs (Last Win)
- 20 / 20 (67%) - No bigger than 63/5 (Career Win)
- 20 / 20 (70%) - Had 1 - 4 wins (180 Days)
- 20 / 20 (70%) - No bigger than 63/5 (Career Place)
- 20 / 20 (71%) - Within the first 9 of the market
- 20 / 20 (71%) - Ran over 1m - 1m1f (Last Win)
- 20 / 20 (71%) - In a field of 4 - 10 (Last Win)
- 20 / 20 (74%) - Ran on FS (Last Win)
- 20 / 20 (75%) - Highest Won is not LST/Cl3
- 20 / 20 (78%) - Ran in USA (Last Win)
- 20 / 20 (80%) - Had 1 - 6 wins (Career)
- 20 / 20 (81%) - No bigger than 27/1 (Career)
Remember to use the trends listed above, along with the Churchill Downs racing predictions, to see if you can find the winner of the Kentucky Oaks. Did you know that we have an OLBG Betting School section on OLBG? It is a place to help you improve your betting experience with articles covering numerous topics.
Are you already a member? If not, then why not? With over £6,000 given away each month in the tipster competition, why not get involved? Remember, it is completely FREE! So, head over to the registration page to sign up today! If you are already a member, then share your thoughts on the Kentucky Oaks by adding a tip on the race here.
101 Ways to find Winners in Horse Racing
Kentucky Oaks Trend Analysis
✅ The trend factor, which has produced 10+ winners and shows the best LSP, an LSP of +55.80, is when runners had 2 wins in the past 180 days.
❌ The worst performing factor that has failed to produce a single winner is when runners had 0 wins in the past 180 days, when backing these, the trend shows a record of 0-76.
Here are the most recent winning draws, along with the further placings in brackets:
- 2026: Winner in 7 (5,4) [13 Runners]
- 2025: Winner in 10 (4,12) [13 Runners]
- 2024: Winner in 4 (12,3) [14 Runners]
- 2023: Winner in 14 (3,2) [14 Runners]
- 2022: Winner in 1 (4,9) [14 Runners]
The courses that have produced the most winners of the Kentucky Oaks are Keeneland and Fair Grounds; there have been a total of 5 winners from each of those courses.
Looking over the past renewals, these are the stallions whose offspring have produced multiple winners of the Kentucky Oaks:
- Medaglia dOro (3 Wins)
- Proud Citizen (2 Wins)
These are the stallions whose offspring have not produced a winner of the Kentucky Oaks despite multiple attempts:
- Unbridleds Song (0 Wins from 5 runners)
- Uncle Mo (0 Wins from 5 runners)
Looking at the winning odds over the last 20 renewals, the biggest-priced winner was Princess Of Sylmar in 2013, winning for Todd Pletcher at odds of 39/1 under the guidance of Mike E Smith. Looking at the runners at the head of the market over the last 20 renewals, there have been 7 winning favourites in the race. Ahead of the 2027 Kentucky Oaks, why not head over to the best racing tipster page to see what the tipsters are backing today? All figures and trends above, such as the horse's previous runs, are based on the information that is available on the Racing Post.
Route to the Kentucky Oaks
Many trainers target races as preparation for the Kentucky Oaks. These are the races which the recent winners ran in before coming here:
| Info | Last Race |
|---|---|
| 2026 - Always A Runner Aqueduct - 1st of 8 (57/10) | Gazelle Stakes |
| 2025 - Good Cheer Fair Grounds - 1st of 8 (2/5) | Fasig-Tipton Fair Grounds Oaks |
| 2024 - Thorpedo Anna Oaklawn Park - 1st of 10 (37/10) | Fantasy Stakes |
| 2023 - Pretty Mischievous Fair Grounds - 2nd of 5 (23/10) | Fair Grounds Oaks presented by Fasig-Tipton |
| 2022 - Secret Oath Oaklawn Park - 3rd of 9 (7/5) | Arkansas Derby |
| 2021 - Malathaat Keeneland - 1st of 6 (6/4) | Central Bank Ashland Stakes |
| 2020 - Shedaresthedevil Indiana Grand - 1st of 8 (8/5) | Indiana Oaks |
| 2019 - Serengeti Empress Fair Grounds - 7th of 7 (3/10) | Twinspires.com Fair Grounds Oaks |
| 2018 - Monomoy Girl Keeneland - 1st of 7 (3/10) | Central Bank Ashland Stakes |
| 2017 - Abel Tasman Santa Anita - 2nd of 7 (19/10) | Santa Anita Oaks Stakes |
Article Contributor Information
We are fortunate to have an excellent team of specialists and experts at OLBG. Contributing to the creation and maintenance of this Kentucky Oaks Preview are Andy and James. They both work on the Horse Racing Tips team, overseeing the tipsters and managing the tip settlement, while also creating and managing all the horse racing event previews for International racing.
James Banting
Expert Guide
Andy Powell
Expert Guide
Other Principal Races in the US
Here are some other notable races throughout the US, which take place during the racing season that we also have blogs for.
Races at Belmont Park Racecourse
Races at Churchill Downs Racecourse
Races at Far Hills Racecourse
Races at Gulfstream Park Racecourse
Races at Pimlico Racecourse
Races at Breeders' Cup World Championships
- Breeders' Cup Classic
- Breeders' Cup Dirt Mile
- Breeders' Cup Distaff
- Breeders' Cup Filly & Mare Sprint
- Breeders' Cup Filly & Mare Turf
- Breeders' Cup Juvenile
- Breeders' Cup Juvenile Fillies
- Breeders' Cup Juvenile Fillies Turf
- Breeders' Cup Juvenile Turf
- Breeders' Cup Juvenile Turf Sprint
- Breeders' Cup Mile
- Breeders' Cup Sprint
- Breeders' Cup Turf
- Breeders' Cup Turf Sprint
