2024 Longines Kentucky Oaks G1 Stakes - Churchill Downs - Picks, predictions, and analysis (GRADE: 70%)

Pick Pony |May 2, 2024, 3:19 p.m.

About the Kentucky Oaks Stakes

Lillies for the Fillies

The Kentucky Oaks is an annual Grade I stakes race for three-year-old Thoroughbred fillies held at Churchill Downs in Louisville, Kentucky, United States. The event was initially run on May 19, 1875, at Churchill Downs, then known as the Louisville Jockey Club. Interestingly, the race was established by Meriwether Lewis Clark Jr., who also founded the Kentucky Derby, the Clark Handicap, and the Falls City Handicap. The Kentucky Oaks and the Kentucky Derby are the most ancient and continuously contested sporting events in American history.

The race covers a distance of 1+1⁄8 miles (1,800 m) and the horses carry 121 pounds (55 kg) during the race. The Kentucky Oaks is held on the Friday before the Kentucky Derby each year. The winner receives $750,000 of the $1,250,000 purse and a beautiful garland blanket of lilies, earning the nickname “Lilies for the Fillies.”

How horses qualify for the Kentucky Oaks

In order for horses to compete in the Kentucky Oaks, they must first go through a qualification process to ensure that they have the necessary talent and credentials. The qualification process for the Oaks is similar to that of the Kentucky Derby, but there are some differences between the two.

In order to be eligible for the Kentucky Oaks, horses must accumulate points by participating in specific Oaks prep races. These races take place from September of the previous year to April of the current year. The point system used is similar to the Kentucky Derby’s, where the top four finishers in each designated race receive points on a sliding scale. In case of a tie, the filly with the highest earnings in graded stakes races will be given priority. The maximum number of horses allowed to start in the Oaks is 14.

Fillies who fail to accumulate sufficient points to qualify for the Oaks can still be considered for entry. If a filly has an exceptional performance or an impressive resume, the racing committee and Churchill Downs officials may extend an invitation to participate in the race. Such invitations are rare and are typically issued when there is a lack of qualified entries.

Kentucky Oaks records

Here are some of the notable records for the Kentucky Oaks horse racing event:

- The fastest winning time in the history of the race is 1 minute and 43.6 seconds over a distance of 1-1/16 miles. This record was set by two horses: Ari’s Mona in 1950 and Sweet Alliance in 1977.
- The fastest winning time at the current race length of 1 and 1/8 miles is 1 minute and 48.28 seconds. This was achieved by Shedaresthedevil in 2020.
- The horse with the largest winning margin in the Kentucky Oaks is Rachel Alexandra, who won by 20-1/4 lengths in 2009.
- The longest shot to ever win the Oaks was Lemons Forever, who had 47-1 odds in 2006.
- Eddie Arcaro and Manuel Ycaza are the jockeys with the most wins in the Kentucky Oaks, with four each. Their last wins were in 1958 and 1968, respectively.
- Rosie Napravnik is the only female jockey to have won the Oaks, achieving this feat twice in 2012 and 2014.
- Woody Stephens and D. Wayne Lukas are the trainers with the most wins in the Kentucky Oaks, with five each. Stephens' last win was in 1981, while Lukas' most recent win was in 2022.
- Calumet Farm is the owner with the most wins in the Oaks, with six victories in 1943, 1949, 1952, 1953, 1956, and 1979.

Prior winners of the Kentucky Oaks

Here are the prior winners of the Kentucky Oaks.



Position after first 1/2-mile

½-mile & ¾-mile times


Pretty Mischievous

5th by 3 lengths (14 starters)

:46.96, 1:11.28 (fast)


Secret Oath

8th by 4.75 lengths (14 starters)

:46.51, 1:11.44 (fast)



5th by 3 lengths (13 starters)

:47.47, 1:11.31 (fast)



2nd by 1 length (9 starters)

:47.92, 1:12.12 (fast)


Serengeti Empress

1st by 3 lengths (14 starters)

:46.65, 1:11.26 (fast)


Monomoy Girl

2nd by 0.5 lengths (14 starters)

:47.70, 1:11.49 (fast)


Abel Tasman

13th by 16.5 lengths (14 starters)

:46.24, 1:11.42 (sloppy)


Cathryn Sophia

4th by 3 lengths (14 starters)

:47.87, 1:12.60 (fast)


Lovely Maria

4th by 2 lengths (14 starters)

:47.26, 1:11.50 (fast)



4th by 2 lengths (12 starters)

:47.80, 1:12.24 (fast)


Princess of Sylmar

9th by 8 lengths (10 starters)

:46.79, 1:11.34 (fast)


Believe You Can

2nd by 1 length (14 starters)

:47.47, 1:11.88 (fast)


Plum Pretty

2nd by 3.5 lengths (13 starters)

:46.99, 1:11.25 (fast)


Blind Luck

14th by 11 lengths (14 starters)

:48.15, 1:12.50 (fast)


Rachel Alexandra

2nd by 1.5 lengths (7 starters)

:47.46, 1:11.81 (fast)


Proud Spell

2nd by 1 length (10 starters)

:48.86, 1:12.95 (sloppy)


Rags to Riches

5th by 2.5 lengths (14 starters)

:47.89, 1:12.69 (muddy)


Lemons Forever

14th by 14 lengths (14 starters)

:46.45, 1:11.47 (fast)



1st by 1 length (7 starters)

:47.44, 1:11.53 (fast)



2nd by 4.5 lengths (11 starters)

:46.00, 1:09.99 (muddy)

Three notable trainers will throw down again in this year’s 2024 Kentucky Oaks run. D. Wayne Lukas achieved his fifth victory in 2022 with Secret Oath. Todd Pletcher has won the Oaks four times, with Malathaat in 2021 joining Princess of Sylmar, Rags to Riches, and Ashado. Brad Cox has won the Run for the Lilies twice with Shedaresthedevil in 2020 and Monomoy Girl in 2018. With several potential win contenders, this year’s Kentucky Oaks promises to be one for the ages.

Of note is that the chance for rain is very high (> 70% at the time of this writeup), which could turn this race on its head.

Bias and outside factors

The Kentucky Oaks generally offers a modest pace (by G1 standards) that favors early runners. Of the last twenty Kentucky Oaks winners, nine were in the first or second positions after the opening half-mile. Fourteen of the last twenty were racing within a few lengths of the lead, indicating the race favors early speed styles. Late-running style winners are rare.

As for post position, 20 of the 60 fillies to make it on the board started in outside posts, beyond lane 10. And that doesn’t take into consideration years where less than 10 runners participated. Similarly, only two fillies in the last 20 years made the board from post 1. Post 2 is almost as bad.

Also, half of the last 20 Kentucky Oaks winners raced at Fair Grounds during the winter. It appears to be the standard proving ground for Kentucky Oaks runners.

2024 Kentucky Oaks entries and analysis

Tapit Jenallie

Tapit Jenallie burst onto the scene by winning her first two starts. She won her maiden, then her first stakes race at Delta Downs before moving to Oaklawn Park to race with the big boys, taking second in the Honeybee (G3) and third in the Fantasy (G2) in her last two races. Her speed, however, is trending downward and her works look lazy, both important considerations given she is one of the slower horses in this group. She could get a boost with a wet track, but likely not enough to matter. Toss.

Gin Gin

Gin Gin is one of two fillies Brad Cox has in this year’s Kentuck Oaks. Most recently, she took a distant third in the Gazelle (G3) at Aqueduct, behind both Where’s My Ring and Regulatory Risk. Her works have peaked at the right time (to be expected, given her trainer is one of the best in this group).

Her speed is trending up, but AI predicts a downward cycle for this race. Although her speed is merely average compared to that of her competitors, she is one of the fastest early runners, which could benefit her given the track bias.

She may prefer a wet track, having turned in one of her fastest races in the mud. If the track is dry, she won’t make it on the board, but if it’s muddy, we think she’ll could be in the money. And we think the track will be muddy.

Where's My Ring

Keep an eye on Where’s My Ring. She moved across the country to win her maiden victory at the Gazelle, then on to Santa Ysabel (Ge) to take second behind Kinza (who is ineligible to run in the Oaks). She really turned the corner when blinkers were added. 

She is easily the fastest horse in this race and has the top early pace numbers, both E1 and E2. Her works have peaked and her speed is improving (although AI predicts she will be a bit slower than her smashing speed rating her last time out). The ROI on the trainer/jockey combo is through the roof.

Given her pedigree, a wet track may not affect Where’s My Ring’s performance. She will likely finish in the money. Odds could make this one attractive.

Regulatory Risk

Chad Brown’s Regulatory Risk took second in the Gazelle at Aqueduct. Although her speed trendline is tilted up, it’s because she produced a speed rating in her last outing, which was far higher than the norm. In fact, her speed rating is generally in the lower third of this group. We must surmise that her speed will return to “normal.”

In this race, the blinkers come off, but we’re not convinced that they will have an impact. She’s already been beaten by several participants in this race, including Where’s My Ring, Gin Gin, and Tarifa. The wet track could negatively impact her performance, too. Her worst speed rating came on a sloppy track.

She’s classified with an early run style. We think this is morphing into a pressing style, which may not benefit her given the track bias for early runners.

We don’t think she’ll make it in the money, but that may not matter anyway. With Chad Brown leading the show and Jose Ortiz in the irons, this may be an underlay.

Thorpedo Anna

Thorpedo Anna has our eye, although if the track is wet, she may flounder. Works have peaked. Speed is trending up, and E1/E2 pace is rising. Her speed is barely in the top five, and most of her other stats are merely average. This is surprising given her excellent finishes and illustrates how stats don’t always tell the whole story.

She won her first two starts, including an allowance at Churchill, and then took second in the Golden Rod (G2). This year, she won her only start in the Fantasy (G2) at Oaklawn. Still, we don’t think she’ll finish in the money. We are presuming the track will be wet, and although she’s never been tested on a muddy track, given her pedigree, we think she will miss the board by a spot or two.

Lemon Muffin

Lemon Muffin took six tries to break her maiden in the Honeybee (G3) at Oaklawn, then plummeted to seventh in the Fantasy.

All pace ratings are rising, but speed is erratic and nearly trending flat. She’s already shown that playing in the mud is fine for her, so adverse weather won’t impact her race. However, that won’t matter. She’s one of the slowest horses in the group. Toss.

Fiona's Magic

Fiona’s Magic broke her maiden convincingly with a seven-length win in her second start at Gulfstream Park. She then moved to graded stakes, where she took second in the Forward Gal (G3) and next won the Davona Dale (G2). She then ran in the Park Oaks (G2), where she was demolished. Trainer Bo Yates said that after the race, she coughed up mucus, which indicates she was ill. As of today, her works have peaked at just the right time.

The disastrous Park Oaks race make her speed rating appear to be trending down. Don’t be fooled. It’s trending flat. A G1-caliber race is slightly out of her range. She will finish around the middle of the group.


Brad Cox’s Tarifa enters this stalker as the favorite. She won her first start at Keeneland by six lengths, then floundered in an allowance at Churchill Downs before gathering her wits and winning her next three races - an allowance, Rachel Alexandra (G2), and Fair Grounds Oaks (G2).

Her works have peaked and have been sharp. Her speed and pace are moderately improving all around. Her post position is great, given the track bias for outside lanes, and Flavien Prat in the irons is a plus. She runs on a wet track as well as a firm one.

However, her running style and lack of speed make her an average entry in this race. She will not finish in the money.


Everland is a rags-to-riches story. She broke her maiden at Turfway Park and was claimed for $30k. She next won a starter allowance and took fourth in her first stakes race. Things looked dire in her run in the Bourbonette Oaks when she inexplicably moved from last to first to take the win.

All of Everland’s pace ratings are climbing, and her speed numbers are trending up sharply. If there were an award for Most Improved, she’d take home the gold. But this is a test of speed, and in that arena, she’s still not up to par. Toss.

Into Champagne

Into Champagne is another filly who won her debut races, the first at Ellis Park and then in a stakes race at Gulfstream. However, this presser could only muster second in the Davona Dale and third in the Gulfstream Park Oaks.

Her speed is trending up but may be beginning to flatten. Her works are meh. She likes getting dirty in the mud, but we think she’s a bit outclassed here. Toss.

Ways and Means

Chad Brown’s second entry in the Kentucky Oaks is Ways and Means. This is the filly that won at Saratoga with a 13-length edge. She took second in the Spinaway (G1) despite many troubles in the race. In her first start of 2024, she again experienced some unexpected issues in the Gulfstream Parks Oaks (G2) but managed to finish second.

Chad Brown has made the necessary corrections, and her works have been very strong. Although untested on the wet stuff, her pedigree hints it won’t be a problem; indeed, she may even prefer it.

Don’t let the downward trending speed and pace alarm you. This filly has heart and wants to win. She could produce an overlay for those going off of stats only and has an excellent chance of making the board and a decent chance of winning, too. Watch the odds and make bank on her if the other bettors screw up. We’re putting her in the Place column.

Power Squeeze

Power Squeeze is riding high on four wins in a row. She won her maiden race at Deleware Park, then won the Cash Run at Gulfstream, the Suncoast at Tampa Bay Downs, and the Gulfstream Park Oaks where she finished ahead of Ways and Means

Her pace numbers are rising and her speed is trending up sharply. She hasn’t been tested at this level but has already demonstrated she can beat Ways and Means and Into Champagne. She’ll run fine on a wet track. She likely will miss the board by a position or two, but watch for an overlay.

Just FYI

Just FYI runs this year’s Kentucky Oaks as one of the favorites, along with Tarifa and Leslie’s Rose, who will be running next to her. She arrives via legendary trainer Bill Mott. She has won all three of her starts, including her debut at Saratoga, the Firzette (G1), and the Breeder’s Cup Juvenile Fillies. She entered the Ashaland (G1) at Keeneland and took second. 

Here last works were unusually off but Just FYI is the second fastest horse in the race, just slightly ahead of Candied and Leslie’s Rose. Wet track? No worries. She easily won the Frizeetee G1 at Belmonnt on a sloppy track.

She is definitely a contender for the board in any G1 race, and her position in the 13th gate is perfect for Churchill Down’s track bias. Rain or not, it’s Just FYI for the win.

Leslie's Rose

Todd Pletcher’s Leslie’s Rose will run as one of the race’s favorites. She won the Ashland (G1) at Keeneland and has a 3 for 4 lifetime record. Her lane has the optimal bias, too. Her excellent late pace may not help her, though. Closers rarely win the Kentucky Oaks.

Her last works was only average and her speed so-so. Hopefully the win in her last race at Ashland will peak the crowd’s interest and an underlay will develop so we don’t have to think too much. Making the board is likely but not guaranteed.

Our Pretty Woman (eligible)

In her latest outing, Steve Asmussen’s Our Pretty Woman took second in the Fair Ground Oaks (G2). If she draws in off the also-eligible list (requires one defection), she could be the early speedster in this race and potentially make it on the board, especially if the track surface is wet. Her latest works have been a bit wonky though. She is our longshot contender.

Candied (eligible)

Todd Pletcher’s Candied took third in the Breeder’s Cup Juvenile Fillies (G1) in 2023. She’ll need two to drop out in order to draw in and would likely do fine on a wet track. An overlay would be interesting.