The Kentucky Oaks began as a companion to the Kentucky Derby Presented by Woodford Reserve, much as the English Oaks at Epsom serves as the female version of the prestigious Derby.

For many years, the Oaks was more of a regional event, a broodmare-maker rather than a show for stars. Also continuously contested since 1875, this run for the lilies has become as much of a destination as the run for the roses, thanks to names like Monomoy Girl, Princess Rooney, and Ashado.

As we celebrate 150 years of the fillies, here are ten Oaks-winning standouts, the best of the best to come home victorious in this distaff test.

Modesty (1884)

This granddaughter of the legendary Lexington originally raced under the name Golden Rod, but when prominent owner Edward C. Corrigan purchased the filly, he renamed her Modesty. On the racetrack, she was anything but modest.

Her stakes wins at age 2 prompted Corrigan to nominate her for both the Kentucky Derby and Oaks and the inaugural American Derby at Washington Park in Chicago. A misunderstanding left her off the list for the 1884 Derby, but she led the list of 50 fillies nominated for that year’s Oaks. On the big day, though, only three others met her at the starting line, the majority scared away by the Corrigan filly. Under legendary jockey Isaac Murphy, Modesty got away to a fast start and had her own way the entire 12 furlongs, her margin of victory estimated as six to 10 lengths.

On June 28, Murphy and the filly faced a field of 11 others at Washington Park for the 1 ½-mile American Derby. The pair raced just off the pace until the stretch, and the filly and three others powered down the straight as a group, Modesty sitting in third as the wire loomed ahead. A fearless Murphy sent her between horses to make one final bid for the lead. At the finish line, her victorious margin was a nose.

Her success on the racetrack followed her into the next phase of her life. As a broodmare, she produced five foals, including Daisy F, making Modesty the great-grandam of Regret, the first filly to win the Kentucky Derby.

Princess Doreen (Keeneland Library Cook Collection)

Princess Doreen (1924)

A daughter of Sir Barton’s half-sister Lady Doreen, Princess Doreen is a throwback to an era when fillies and mares would race more often in open company since the distaff division had fewer stakes. The daughter of Spanish Prince II started with early wins in allowance and maiden races at 2 with no stakes wins prior to her try in the Kentucky Oaks, although she did finish second by a nose in the Fort Thomas Handicap to Chilhowee, who would then finish second to Black Gold in the 1924 Derby. Her competition for the 1924 Oaks would include fillies like Glide, a stakes winner also nominated for the Derby, and Nellie Morse, who had beaten colts in the Preakness in early May.

On Churchill’s closing day for the spring meet, eight fillies went to the starting line for the 1 1/8-mile stakes. Coming out of the far turn, both Nellie Morse and Princess Doreen made their bids for the lead as the field straightened for home. Glide made a furious move in the straight as she passed Nellie Morse first and then ran down Princess Doreen to win by two lengths. However, the stewards thought the filly had interfered with multiple horses during her stretch run and disqualified her to third, giving Princess Doreen the victory, a first for the Oaks.

Princess Doreen added the Coaching Club American Oaks later that season and then beat the males in races like the Autumn, Covington, and Saratoga Handicaps over the next three years. Her 34 wins in 94 starts, including the Kentucky Oaks, earned the daughter of Lady Doreen a spot in the Hall of Fame.

Black Maria (Keeneland Library Cook Collection)

Black Maria (1926)

Owner William R. Coe gave his daughter of Black Toney the moniker Black Maria after a legendary four-mile mare from the early 19^th century. At first, the filly bred by Col. E. R. Bradley’s Idle Hour Farm did not resemble her namesake, as her inability to break well prevented her from realizing her potential. But at age 3, Black Maria put it all together to discover her winning form.

After finishing fourth in the Wood Stakes (later Wood Memorial), Black Maria was third behind Rapture in the Pimlico Oaks and then won the Ladies Handicap before making the trip to Churchill Downs for the Kentucky Oaks. As the field of 10 made its way from the paddock to the racetrack, the skies opened up and poured rain so hard that the crowd could not see the horses and every jockey came back soaked with mud. At the wire, Black Maria was four lengths in front with Rapture far back in seventh. She added wins in the Aqueduct Handicap, the Illinois Oaks, and others during her 1926 season.

Racing at 4 and 5, Black Maria added another Ladies Handicap, a victory against open company in the Metropolitan Handicap, and then won the inaugural Whitney Stakes at Saratoga. As a broodmare, she produced only one foal, Black Queen, before being euthanized after a paddock accident at age 9. Black Queen would pass her dam’s excellence on to a series of foals, including Black Polly, the dam of Preakness winner Polynesian, the sire of Native Dancer.

Cicada under Bill Shoemaker (Keeneland Library Morgan Collection)

Cicada (1962)

A homebred for Christopher Chenery’s Meadow Stables, Cicada was as talented as her stablemate Sir Gaylord, who was set to carry the famed blue and white silks on Derby day. She was nominated to both the Oaks and the Derby, but Chenery and trainer Casey Hayes opted to send her to the Oaks. Sir Gaylord’s injury on Derby morning would keep him out of that race, but Cicada’s Oaks victory was another in a long list of wins for the filly.

At 2, she started 16 times, winning eight stakes including the Frizette and the Spinaway. After finishing second to Ridan in the Florida Derby, she won the Oaks Prep at Churchill Downs six days before her chance at lilies. The field was small, only six horses, and Cicada won easily over Flaming Page, a future Queen’s Plate winner and eventual Canadian Hall of Famer. The remainder of her 1962 season would see her win the Acorn, Mother Goose, and Beldame Stakes.

A stifle injury cut short her 4-year-old season, sending her to Chenery’s Meadow Stud for broodmare duty, but when she did not get in foal, he sent her back to the racetrack. She was fourth in her lone race that season and then retired for good. Cicada’s excellence on the racetrack earned her championship honors in 1961, ’62, and ’63 then a spot in the Hall of Fame a few years later.

Dark Mirage winning 1968 CCA Oaks (NYRA photo)

Dark Mirage (1968)

Great horses do come in small packages, as evidenced by Hall of Famer Dark Mirage. Barely 14 hands and 700 pounds when purchased as a yearling, the petite filly did not get her first stakes win until her turn in the Prioress at Aqueduct in early April. She was unbeatable from that point forward.

In the La Troienne at Churchill Downs, she laid off the pace until the stretch and then easily took the lead to win by three lengths. Six days later, she was back for the Kentucky Oaks, weaving through a crowded field of 14 to take the lead with a rush at the eighth pole before drawing off to win by 4½ lengths. Dark Mirage then returned to New York for the Acorn Stakes, Mother Goose Stakes, and Coaching Club American Oaks, locking up the Filly Triple Crown with wins in each race, the final two by double-digit margins. Her Delaware Oaks only attracted three other fillies to race against her, making the race a non-betting event.

A foot injury in the Delaware Oaks ended Dark Mirage’s 3-year-old season early; she recovered enough to return the following February in winning the Santa Maria Handicap. In her next start, the Santa Margarita Handicap, another horse bumped into her at the start, causing her to dislocate a sesamoid in her right front fetlock. She was immediately retired, but the injury never healed. Emergency surgery did not resolve the issue and laminitis set in, necessitating an early end to Dark Mirage’s life. Her accomplishments were enough to earn her champion 3-year-old filly honors and a spot in the Racing Hall of Fame.

Susan's Girl (BloodHorse Library/Bob Coglianese photo)

Susan's Girl (1972)

Fred W. Hooper won the 1945 Kentucky Derby with the first horse he purchased, a son of Sir Gallahad III he named Hoop Jr. While he pursued another Derby victory for the next six decades, the Florida breeder did find success under the Twin Spires with his three Oaks victories, with My Portrait in 1961 and Quaze Quilt in 1974. In between those two was another Hooper homebred, Susan’s Girl.

Bred by Fred Hooper Jr. and named for his wife, Susan, the elder Hooper bought the daughter of Belmont Stakes winner Quadrangle from his son and raced her in his red, white, and blue silks. She was a multiple stakes winner in her juvenile season and then started her 3-year-old season with a trio of stakes wins in California. She prepped for the 1972 Kentucky Oaks with a win in the La Troienne Stakes and then faced six others in the run for the lilies.

Normally amenable to racing off the pace, Susan’s Girl had a mind of her own in the 1 1/16-mile Oaks, jockey Victor Tejada ceding control to the filly early in the race. Her steady stride left her enough in reserve to hold off a closing Barely Even by a length.

She raced for three more seasons and maintained a high level of achievement each of those years. Susan’s Girl was twice a winner of the Delaware Handicap as well as the Spinster and Beldame Stakes and became the first North American distaffer to win $1 million. Her long list of achievements earned her a spot in the Racing Hall of Fame in 1976.

Davona Dale with trainer John Veitch (BloodHorse Library/Photo Communications)

Davona Dale (1979)

Calumet Farm not only holds the record for Kentucky Derby wins with eight but also the record for the Kentucky Oaks with six. Their first, Nellie L., was a daughter of their first Derby starter, Nellie Flag, and three and a half decades later, the final Oaks victor in the devil red and blue silks was a homebred star named Davona Dale.

Named for a character in one of Admiral Gene Markey’s novels, the Best Turn filly won both of her starts at 2 before going on to a 3-year-old season to remember. After finishing fourth against males in the Tropical Park Derby and second sprinting in the Shirley Jones Stakes, Davona Dale went on an eight-stakes winning streak, winning at six different racetracks from late February to late June. Those eight included the Kentucky Oaks, in which she defeated a short field of just five opponents, including Candy Éclair, the 1978 champion 2-year-old filly.

After her Oaks win, Davona Dale captured the Black-Eyed Susan, Acorn and Mother Goose Stakes then the Coaching Club American Oaks, giving the Calumet filly not only the Filly Triple Crown but also the New York Triple Tiara. Her stellar 1979 season earned her the Eclipse Award  as champion 3-year-old filly and then a spot in the Hall of Fame alongside a plethora of Calumet champions.

Open Mind (BloodHorse Library/Bob Coglianese)

Open Mind (1989)

Eugene Klein’s second half of the 1980s was one for the record books. His champion mare Lady’s Secret was 1986 Horse of the Year after defeating open company in the Whitney Handicap and then winning the Breeders’ Cup Distaff. Then, Winning Colors gave Klein his only Kentucky Derby win with her wire-to-wire performance in 1988. A year later, Open Mind brought the Californian another historic victory at Churchill Downs in the 1989 Kentucky Oaks.

After sealing her 2-year-old championship in the Breeders’ Cup Juvenile Fillies, the daughter of Deputy Minister went on to win her next four races before joining four others in the starting gate for the Kentucky Oaks. In the stretch, Open Mind moved around stablemate Imaginary Lady to take the lead and win by 2 ¼ lengths. She followed that with wins in the Acorn and Mother Goose Stakes before finishing second to Nite of Fun in the Coaching Club American Oaks, whose disqualification gave Open Mind the win and the New York Triple Tiara. She added the Grade 1 Alabama to her list of stakes wins in her 3-year-old season, sealing her second Eclipse Award and earning her a spot in the Racing Hall of Fame.

Rags to Riches after 2007 Oaks (Anne M. Eberhardt/BloodHorse)

Rags to Riches (2007)

The Kentucky Derby has had three, the Preakness six, and the Belmont Stakes only three – victorious fillies that is. The winner of the first Belmont in 1867 was Ruthless, and then nearly four decades later, Tanya in 1905 became the second filly to take this classic race and the first to do it at Belmont Park. It would be another century until Rags to Riches, a third-generation winner of the ‘Test of the Champion,’ added her name to that short list following in the footsteps of sire A.P. Indy and his sire, 1977 Triple Crown winner Seattle Slew. Before that classic run, the chestnut daughter of A.P. Indy had her run at another marquee win in the Kentucky Oaks.

She raced only once at 2 and then started her 3-year-old season with three wins at Santa Anita Park before shipping east to Churchill Downs. The field for the 2007 Oaks was a full 14, including Dreaming of Anna, winner of the previous year’s Breeders’ Cup Juvenile Fillies. Rags to Riches and jockey Garrett Gomez entered the starting gate as the favorite and bounded home to an easy 4 ¼-length victory. On a four-race win streak, owners Michael Tabor and Derrick Smith and trainer Todd Pletcher decided to take a chance and send their filly in the Belmont Stakes.

She was one of seven entered for the Belmont Stakes, joined by Preakness winner Curlin and Derby runner-up Hard Spun. Rags to Riches stumbled at the start, but jockey John Velazquez coolly helped her recover and horse and rider patiently bided their time throughout the stamina-testing 1 ½ miles. On the far turn, Hard Spun, Curlin, and Rags to Riches hooked up and swung into the stretch together. Rags to Riches angled toward the rail after passing Hard Spun and dueled with Curlin through the stretch, gaining a short advantage over the Preakness winner and holding off his late charge to win by a head.

Unfortunately, the Belmont winner injured her right front pastern in her next start, the Gazelle Stakes at Belmont, and did not race again. Despite her short career, Rags to Riches is among the most distinguished winners of the Kentucky Oaks, the only one to add the Belmont Stakes to her résumé. Two years later, she would be joined by another elite distaffer, one who made her own classic impact in an elite career.

Oaks domination by Rachel Alexandra (BloodHorse/Mike Corrado)

Rachel Alexandra (2009)

Few names elicit instant recognition for modern racing fans: A.P. Indy, Zenyatta, American Pharoah, and of course, the filly who ‘raised the rafters at the Spa,’ Rachel Alexandra.

The Kentucky Oaks has seen its share of famed fillies win this classic in its 150 years, a literal litany of Hall of Famers and Eclipse champions, but in 2009, the run for the lilies had one of its most popular winners yet. A graded stakes winner at age 2, the daughter of Medaglia d’Oro started her 3-year-old season with wins in the Martha Washington Stakes, Fair Grounds Oaks, and Fantasy Stakes.

In the Kentucky Oaks at Churchill Downs, Rachel Alexandra met six other fillies and put on a show that might have won the Kentucky Derby had she been entered. With Churchill-based Calvin Borel in the irons, Rachel Alexandra patiently stalked early leader Gabby’s Golden Gal before effortlessly taking the lead in the far turn and cruising to an incredible 20 ¼-length win, an Oaks record.

In the two weeks between the Oaks and Preakness weekend, Jess Jackson of Stonestreet Farm and Harold McCormick paid $10 million for Rachel and switched her from trainer Hal Wiggins to Steve Asmussen. She then faced Kentucky Derby winner Mine That Bird and Pioneerof the Nile, sire of Triple Crown winner, American Pharoah, plus 10 others in the Preakness Stakes, with Borel choosing to stay aboard Rachel Alexandra after riding Mine That Bird to an upset win in the Derby. The talented filly went into the gate as the favorite and held off a closing Mine That Bird to become the first filly since Nellie Morse in 1924 to take the middle jewel of the Triple Crown.

The rest of her 3-year-old season saw Rachel Alexandra beat the boys again in the Haskell Invitational Stakes and then defeat older horses in a rousing performance in the Woodward Stakes at Saratoga. At year’s end, she was voted Horse of the Year – receiving more votes than the undefeated Zenyatta – as well as champion 3-year-old filly. Retired after her 4-year-old season, Rachel Alexandra produced two foals, Jess’s Dream and Rachel’s Valentina, before being pensioned from broodmare duty. This famed Kentucky Oaks champion remains a popular attraction at Stonestreet Farm, which hosts special “Meet Rachel” days for her fans.