In the fall of 1988, Winning Colors finished second to Ogden Phipps' filly Personal Ensign in the Maskette Stakes. The two fillies next met in the Breeders' Cup Distaff at Churchill Downs. Winning Colors had the lead with 10 yards to go when Personal Ensign, who had struggled throughout the race because of the sloppy track, rallied and won by what the U.S. Racing Hall of Fame describes as a "lip." After the race, Winning Colors' trainer, D. Wayne Lukas, said that she had run the best race of her career.