Tyler Gaffalione rode his first winner in the third race of his career on September 7, 2014, at
Gulfstream Park. A track that became a favorite, on May 3, 2015, he won five races on a single Gulfstream Park racecard then on July 4, 2017, he tied
Hall of Fame jockey
Jerry Bailey's 19-year-old record by winning seven races on a single Gulfstream Park racecard. On June 30, 2018, Tyler Gaffalione captured his sixth riding title at
Gulfstream Park. In 2018, Tyler Gaffalione was riding primarily at Gulfstream Park and
Saratoga Race Course. He earned his first Grade I victory in the
La Troienne aboard Salty and finished in eleventh place in the National Earnings list. In 2026, he rode late-qualifier Ocelli to a surprise third place finish in the
2026 Kentucky Derby. ==Year-end charts==