Winning Colors was bred by Echo Valley Farm near Georgetown, Kentucky owned by Donald & Shirley Sucher.

[5] Racing on the West Coast of the United States for trainer D. Wayne Lukas, Winning Colors won both of her starts at age two.

Sent to Churchill Downs for the 1988 Kentucky Derby, she was up against a stellar field of colts including Risen Star, Seeking the Gold, Forty Niner, Regal Classic, and co-favorite Private Terms.

In the fall of 1988, Winning Colors finished second to Ogden Phipps' filly Personal Ensign in the Maskette Stakes.

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.