The 1988 Kentucky Derby was the 114th running of the Kentucky Derby. The race took place on May 7, 1988, with 137,694 people in attendance. Let me take you back to May 7, 1988, the exact day that jockey Gary Stevens and Winning Colors won the Kentucky derby. Winning colors became the only third filly in history to win the Kentucky derby. Also winning colors was inducted into the racing hall of fame in 2000. Some people saw winning colors as an unlikely candidate to end the streak, even though it was clear that she had the talent to win the Kentucky derby.