His success led him to move north to compete on the Maryland racing circuit, where his winning record earned him the Eclipse Award for Outstanding Apprentice Jockey in 1987. While racing in Maryland from 1987-89, Desormeaux won more races than any other jockey in North America. He is one of only four jockeys to have won three national titles in a row. In 1987, he had 450 wins from 2,207 starts with earnings of $5.1 million. In 1988, he improved to 474 wins from 1,897 starts and earnings of $6.3 million. He got his first mount in the Kentucky Derby in 1988, finishing 16th.