Lilies for the Fillies: Kentucky Oaks Winners In Horse Country

2024 – Thorpedo Anna

Starting off with our most recent winner, Thorpedo Anna led the whole way in her Oaks triumph over a sloppy track in lasts year’s edition of the Oaks. She drew well clear of the field during the stretch run with jockey Brian Hernandez Jr. aboard, giving him and trainer Kenny McPeek their first Oaks victory. McPeek would go on to win the Kentucky Derby the very next day, becoming the first trainer to sweep the Oaks/Derby double since Ben Jones in 1952.

After her Oaks triumph, Thorpedo Anna went on to win four G1 races, including the Breeders’ Cup Distaff before being crowned Champion Horse of The Year with the Eclipse Awards at the end of 2024. She spent some time off at Kenny McPeek’s Magdalena Farm in Lexington, Kentucky, before starting her 4-year-old campaign in 2025.

Fun Fact: Thorpedo Anna makes her return to Churchill Downs on Friday, May 2, when she headlines a field of seven fillies and mares for the 40th running of the $1 million Fasig-Tipton La Troienne on the undercard of the Kentucky Oaks!

2023 – Pretty Mischievous

In a thrilling stretch run, Pretty Mischievous held on to win by a neck over Gambling Girl to hand trainer Brendan Walsh, owner/breeder Godolphin, and jockey Tyler Gaffalione their first win in the Kentucky Oaks.

Pretty Mischievous went on to become Eclipse Champion 3-Year-Old Filly by the end of 2023 after picking two more G1 wins and eventually retired to Godolphin’s Gainsborough Farm to become a broodmare for the international racing and breeding operation.

2022 – Secret Oath

Secret Oath surged ahead to win the Kentucky Oaks, becoming the first Kentucky Oaks winner for owner/breeder Briland Farm and jockey Luis Saez. As for her Hall of Fame trainer D. Wayne Lukas, he collected his fifth Oaks win at the age of 86.

Secret Oath finished her on-track career before being sold for $3 million on at the 2023 Fasig-Tipton November Sale. Now residing at Spendthrift Farm, Secret Oath had her first foal, a filly by Into Mischief earlier this year. While she is not available to visit on tours, she is enjoying her second career as a broodmare.

Fun Fact: Spendthrift Farm has also confirmed that Secret Oath has been bred back to Into Mischief for a full sibling to this beautiful filly!

2019 – Serengeti Empress

Sent off at odds of 13-1, Serengeti Empress soared to victory, marketing the first Kentucky Oaks win for her trainer Tom Amoss and jockey Jose Ortiz. It was also owner Joel Politi’s first Oaks win after he purchased Serengeti Empress for $70,000 at the 2017 Keeneland September Yearling Sale.

Serengeti Empress eventually retired at the end of her 4-year-old campaign, which included a win in the GI Ballerina Stakes at Saratoga Race Track in New York. She also finished third in the 2019 Breeders’ Cup Distaff, and second in the 2020 Breeders’ Cup Filly and Mare Sprint.

Now boarded at Taylor Made Farm, Serengeti Empress has adjusted well into her broodmare career and is a highlight on tours from time to time.

Fun Fact: Serengeti Empress’ first foal, Invictus, won his first race in his second start at Keeneland earlier this spring after being sold for $1.2 million as a yearling at the 2023 Keeneland September Yearling Sale!

2018 – Monomoy Girl

After working out a stellar trip under the heady handling of jockey Florent Geroux, Monomoy Girl unleashed a combination of brilliance and guts when she dug down deep to fight off Wonder Gadot in the stretch and survived a subsequent objection to capture the Kentucky Oaks for her connections. Owned by Michael Dubb, Sol Kumin’s Monomoy Stables, The Elkstone Group and Bethlehem Stables, the chestnut filly was purchased for $100,000 at the 2016 Keeneland September Yearling Sale.

Monomoy Girl gave trainer Brad Cox the first G1 win of his career in the G1 Ashland Stakes at Keeneland a month prior to the Oaks, and doubled up on the first Friday in May to give him his first Oaks victory.

Monomoy Girl went on to become a two-time Eclipse Award winner and seven-time G1 winner before officially retiring from racing in 2021. She is now well into her broodmare career at Spendthrift Farm alongside their other Kentucky Oaks winner Secret Oath.

Fun Fact: Monomoy Girl’s first foal, a 2-year-old colt by Into Mischief named Provenance will be raced under Spendthrift Farm and she also has a gorgeous yearling filly by Into Mischief!

2017 – Abel Tasman

Abel Tasman was ridden under Mike Smith and kicked into another gear in the stretch in the Kentucky Oaks to score her second G1 victory. Along with her impressive win, her Hall of Fame trainer Bob Baffert received his third Oaks victory while Mike Smith received his second Oaks victory.

Owned by the China Horse Club and Clearsky Farms, Abel Tasman went on to win four additional G1 races and was named Eclipse Champion 3-Year-Old Filly by the end of 2017. She eventually retired and was purchased for $5 million at the Keeneland January Horses of All Ages Sale by M.V. Magnier.

Abel Tasman now resides at Coolmore America as a broodmare, however she is not accessible on tours.

2016 – Cathryn Sophia

Cathryn Sophia came from off the pace to win the Kentucky Oaks in impressive style, ridden by Javier Castellano for trainer John Servis. Her win in the Oaks was the first for her owner, Chuck Zackney’s Cash Is King LLC, as well as for both Castellano and Servis.

The star-studded filly went on to be named Maryland-bred Horse of the Year, Champion 3-Year-Old Filly and Champion Sprinter in the annual poll conducted by the Maryland Horse Breeders Association at the end of 2016. She became one of only three Maryland-breds in history to become a millionaire at age 3.

Catheryn Sophia eventually retired at the end of 2016 and was purchased by SF Bloodstock for $1.4 million at the Fasig-Tipton November Sale. She now resides at Coolmore America as a broodmare, however she is not accessible on tours.

2012 – Believe You Can

Jockey Rosie Napravnik became the first woman rider to win the Kentucky Oaks when she rode Believe You Can to a historic victory over Broadway’s Alibi. Owner Brereton C. Jones and trainer Larry Jones visited the Oaks winner’s circle for a second time after the pair won with Proud Spell in the 2008 Kentucky Oaks.

Believe You Can then retired to Bereton C. Jones’ Airdrie Stud to start her broodmare career. She is currently not available to see on tours.

2009 – Rachel Alexandra

In spectacular fashion, Rachel Alexandra dominated in the Kentucky Oaks, drawing off down the lane to win by a staggering 20 1/4 lengths. The impressive filly was ridden by Calvin Borel and her win gave trainer Hal Wiggins his first G1 win in 40 years of training racehorses. Rachel Alexandra was soon purchased privately by Jess Jackson and Harold T. McCormick from her previous owners Dolphus Morrison and Mike Lauffer when her success on the track attracted attention. Trainer Steve Asmussen took over from Wiggins later in 2009.

By the end of her racing campaign, Rachel Alexandra would be crowned Champion Horse of The Year with the Eclipse Awards along with Champion 3-Year-Old Filly. Her most notable achievements on track included defeating the males in the G1 Preakness, G1 Haskell Invitational, and G1 Woodward Stakes.

Rachel Alexandra retired near the end of 2010 to become a broodmare at Jess Jackson’s Stonestreet Farm. She is now available to visit from time to time on tours.

Fun Fact: Rachel Alexandra produced two foals in her broodmare career, Jess’s Dream and Rachel’s Valentina, before officially retiring from breeding!

2007 – Rags to Riches

With a late surge to the front, Rags to Riches came out on top to win the Kentucky Oaks with jockey Garrett Gomez aboard. The chestnut filly was purchased by owners Michael Tabor and Derrick Smith for $1.9 million at the Keeneland September Yearling Sale back in 2005. Her win gave Hall of Fame trainer Todd Pletcher his second Oaks win at the time.

Rags to Riches’ 3-year-old campaign continued with a historic win when she became only the third filly to win the Belmont Stakes, and the first to do so in 102 years, fighting hard down to the wire to defeat Curlin by the narrowest of margins. The chestnut filly’s Belmont Stakes victory also gave Pletcher his first Triple Crown race win.

After earning Eclipse Champion 3-Year-Old Filly, Rags to Riches went on to retire in 2008 to Coolmore America, which is where she resides as a broodmare. She is currently not included on tours.

2004 – Ashado

As the favorite in the betting pool, Ashado was unfazed by a muddy track as she pressed the early pace then edged clear to win over Island Sand in the Kentucky Oaks. The filly’s win was the first Oaks win for her Hall of Fame trainer Todd Pletcher at the time. After continuing her impressive campaign as a 3-year-old in 2004, Ashado then provided Pletcher with the first of his 14 Breeders’ Cup wins when she captured the 2004 Distaff and, in the process, became the first filly to win the Kentucky Oaks and the Distaff in the same year.

Ashado was originally purchased by Jack Wolf’s Starlight Stable in partnership with Paul Saylor and Johns Martin at the Keeneland September Yearling Sale for $170,000. Ashado eventually ended her racing career with 12 wins out of 21 starts, and was named both Eclipse Champion 3-Year-Old Filly and Champion Older Female.

The next stage of her career came in November of 2005 at the Keeneland November Breeding Stock Sale, where she was purchased for $9 million by Godolphin. She was officially pensioned from broodmare duties in 2022 after producing a total of 13 foals. Currently, Ashado resides at Gainsborough Farm alongside their other Kentucky Oaks winner Pretty Mischievous and is a very frequent visitor on tours.