On This Date in Sports May 7, 1988: Colorful Filly

In collaboration with the Sportsecyclopedia.com

Winning Colors earns the roses as she becomes just the third filly to win the Kentucky Derby. Trained by D. Wayne Lukas and ridden by Gary Stevens, both earning their first win at Churchill Downs. After a stunning win in Santa Anita, Winning Colors was one of the favorites in Louisville. In winning the derby, she had to hold off a late charge from Forty Niner to win by a neck.

It is rare that a filly can run with the colts, as they often have their own races, as often the best fillies run in the Kentucky Oaks the day from the derby. However, occasionally there is a filly strong enough to run with the colts. Winning Colors was one of those dashing dames with enough stamina, strength, and speed.

Trained in California by D. Wayne Lukas, Winning Colors showed right away she was one special filly when she won her first two races as a two-year-old. She became an attention-getter when she won the Santa Anita Stakes by seven and a half lengths. Despite her amazing win, she was not considered the favorite in the Kentucky Derby as only two fillies had won previously, Regret in 1915 and Genuine Risk in 1980.

  
While she was not the favorite, Winning Colors was a popular bet and a fan favorite in the 114th run for the roses. With Gary Steven in the saddle, Winning Colors raced to the front early as she often did in big races. Holding the lead most of the race, Winning Colors had to hold off a late challenge from Forty Niner, the horse trained by Woody Stephens and ridden by Pat Day, who was one of the betting line favorites despite drawing the 17th gate, in a field of 17 horses. As the mile and a half race was completed, Winning Colors had the winning time of 2:02.20, beating Forty Niner by a neck, while Risen Star, a sire of Secretariat, finished third.
Winning Colors' attempt to become the first filly to win the Triple Crown came to an end in the Preakness Stakes, when she finished third, behind Risen Star and Brian’s Time. Risen Star, who was ridden by Eddie Delahoussaye and trained by Louis Roussel III, would also win the Belmont Stakes while Winning Colors finished last in the field of six horses.

    

  
There have been five fillies in the history of the Preakness to win Preakness Stakes, Flocarline in 1903, Whimsical in 1906, Rhine Maiden in 1915, Nellie Morse in 1924, and Rachel Alexandra in 2009. In the Belmont Stakes, there have been three filly winners, Ruthless who won the inaugural race in 1867, Tanya in 1905, and Rags to Riches in 2007.
It is unlikely another filly will win the Kentucky Derby. Since Winning Colors, only five fillies have attempted to win the Run for the Roses, since 1988 with the Kentucky Oaks becoming a major stakes race in its own right, with Eight Belles coming closest to a win by finishing second in 2008. A new rule put in place in 2013 stating that horses entering the derby needed a certain amount of qualifying points, making it nearly impossible for a filly to qualify for the race.