Detroit Sports Center Detroit Sports Center Home News > Kentucky Derby History? Kentucky Derby History? Posted on 5/2/2014 8:18:00 AM Rob Carr/Getty Anna Rose Napravnik is looking to make history tomorrow during The Greatest Two Minutes in Sports. The 26-year-old will try to become the first woman to ride a Kentucky Derby winner. Her mount in the Derby on Saturday is 20-1 long shot Vicar’s In Trouble. She drew the dreaded No. 1 spot in the starting gate. Napravnik was the highest-placing female rider in the Kentucky Derby, finishing fifth last year aboard Mylute.