 In 1996, he won his first riding title at Aqueduct and also rode his first Eclipse Award winner, Yank's Music, trained by his father-in-law, to Championship Three-Year-Old Filly honors.In 1998, Velazquez won the first of five riding titles at Saratoga.Later that year, he picked up a ride in the Breeders' Cup Mile on Da Hoss, who had won the 1996 Mile but had only raced once in the intervening years.