Trying for Lilies and Roses: Fillies Who Ran in the Kentucky Derby and Won the Kentucky Oaks

When Meriwether Lewis Clark Jr. decided to bring a race akin to the Derby at Epsom to Kentucky, he knew that he needed a similar race for the fillies, modeled on the Oaks at Epsom, as a companion test for the distaff division. Originally contested at 1 1/2 miles, the Kentucky Oaks was carded for the last day of the spring meeting while the Kentucky Derby was the opening day feature.

Because these two stakes were once run at different points on Churchill Downs’ spring calendar, fillies were able to run for roses in the Derby and then days later, go for the lilies too. In its 150 years, five fillies were able to win the Kentucky Oaks after their turn in the Kentucky Derby, putting these distaffers in a class of their own. 

Flamma (1912)

Her sire Hastings won the Belmont S. for August Belmont II and later became the sire of Fair Play, who in turn produced the 20th century’s greatest racehorse in Man o’ War. Her damsire Rayon d’Or was an English classic winner in 1879, taking the 1 3/4-mile St. Leger. Flamma had quality on both top and bottom of her pedigree and she ran true to both.

After logging six wins and four seconds in 33 starts at age two, Flamma was one of only a handful of horses to enter the 38th Kentucky Derby, where she faced the favorite Worth and five others over a muddy track. With future Hall of Famer Johnny Loftus in the saddle, she acted up at the starting line, which cost her the break, and then ran last for the first half-mile before making up ground with a rush to finish third. Two weeks later, she was back at Churchill Downs for the 1 1/16-mile Kentucky Oaks. She ran toward the back of the field early, made up ground on the backstretch, and then took the lead entering the stretch to win by two lengths. 

Flamma would add the Ladies H. to her tally at age four but died of pneumonia before the start of her five-year-old campaign the following year. 

Bronzewing (1914)

Racing primarily in Kentucky, Bronzewing had fewer opportunities to make a name for herself than she would have had in New York and Maryland, but her record shows that she held her own. A daughter of 1903 Champagne S. winner Stalwart, the chestnut filly was one of two to face juvenile star Old Rosebud and four other colts and geldings in the 1914 Kentucky Derby. She entered the race off of wins in both the Ashland Oaks and the Blue Grass S. at the Kentucky Association track in Lexington and then came to Louisville as a serious contender for the 40th Derby. She ran last early and then closed with a furious drive to finish third.

Two weeks later, Bronzewing returned to the starting line to face a field of nine others in the Kentucky Oaks. Her performance echoed the Derby, racing last in the first half of the 8 1/2-furlong contest before moving through the field steadily and then eking out the win in the final strides. Bronzewing would finish her career with a record of 41-6-8-10, the Kentucky Oaks her best win. 

Viva America (1918)

The 1918 Kentucky Derby might be best known for its winner Exterminator, the Hall of Famer who ultimately started in 100 races and won 50 times. The race also featured War Cloud, the first horse to compete in all three of what would become the Triple Crown classics, and the stakes-winning filly Viva America.

She raced primarily in the Midwest, going between Kentucky tracks like Douglas Park, Latonia, and the Kentucky Association track, finishing her juvenile season with eight wins in 12 starts. Viva America entered the Derby as the first filly to compete in the race since Regret became the first distaffer to claim the Run for the Roses three years earlier. Like Exterminator, she was a longshot, going off at 29-1, and claimed the lead from the start, attempting to go wire-to-wire in the 10-furlong test. Her early speed gave out, though, and she finished nine lengths back of a winning Exterminator and Escoba in second. 

Two weeks later, Viva America used her early speed to take the Kentucky Oaks in hand early and never relinquished her advantage. That win made her sire McGee, who had also sired Exterminator, the second stallion to sire both an Oaks and Derby winner in the same year after King Alfonso in 1885 (Joe Cotton and Lizzie Dwyer). 

Startle (1922)

Her grandsire Sunstar and damsire Ayrshire were both dual English classic winners, and her sire Star Hawk was second in the 1916 Kentucky Derby, giving Startle a strong grounding in winning at a distance of a mile and more. She showed her quality at age two, winning five of 10 starts including the Kentucky Jockey Club S. At three, she was second in the Ashland Oaks and third in the Blue Grass S., both at the Kentucky Association track in Lexington, before shipping to Louisville for the 48th Kentucky Derby.

On May 13, she faced the undefeated colt Morvich and a field of eight others, going to the starting line as the race’s lone filly. She was in the front three early in the 10-furlong test but faded to finish sixth behind the victorious Morvich. Three weeks later, she was once again at the Churchill Downs starting line, this time for the nine-furlong Oaks. Pressed by Martha Fallon throughout the race, Startle was able to hold off her rival to win the 48th Oaks by a length. 

Alcibiades (1930)

A homebred for Hal Price Headley, Alcibiades was a good two-year-old, winning four of seven races including a second behind the colt Desert Light in the Kentucky Jockey Club. Her success was expected to carry over to her three-year-old season, but she went unplaced in her first three starts before winning the 6 1/2-furlong Lilies of the Valley Purse three days before the Kentucky Derby. She joined 14 colts and geldings in the starting gate – 1930 was the first year that the Derby used one – and came out swinging, briefly showing her head in front at the half-mile mark before tiring to finish 10th behind Gallant Fox. Alcibiades followed up her Derby performance with a try at the Kentucky Oaks two weeks later. 

Her poor performances earlier in the season had bettors doubting her abilities, but a smaller field and weaker competition meant an opportunity for the Headley filly to shine. She took the lead from the break, gave it up briefly at the half-mile mark, and then rallied to win by a length. An injury in the Latonia Championship cut short her racing career, but as a broodmare, she was brilliant. Her best son Menow went on to sire Preakness and Belmont winner Capot and Hall of Famer Tom Fool.

Alcibiades would be the last filly to compete in the Kentucky Derby and win the Kentucky Oaks. In 1944, the Oaks shifted to the first Friday in May, settling into its now-familiar spot on the calendar. While fillies have tried the Kentucky Derby since then, with two winners in Genuine Risk and Winning Colors, no filly has started in the Run for the Roses since Devil May Care in 2010. That these five remarkable fillies from an earlier time were able to compete in both and win one underscores their extraordinary talent and versatility on the racetrack.