An Associated Press news release at the time of his death called him "one of the most promising young jockeys in the country."
Born in London, Kentucky, Roy Gilbert was one of nineteen children. In 1957 he began riding professionally but in June 1958 was sidelined for a time after he suffered a broken leg as a result of being thrown from his horse during a race at Monmouth Park Racetrack in Oceanport, New Jersey. On April 4, 1961 at Aqueduct Racetrack in Queens, New York, Roy Gilbert was thrown from his horse during the fourth race and struck his head on the concrete base of a rail post.
He died on the way to hospital.
He was a few months shy of his twenty-third birthday.