In 1954, Ray York earned the most significant win of his career when he rode Determine to victory in the Kentucky Derby. In his only appearance in the Preakness Stakes, in 1952 York rode Armageddon to a tenth place showing. In 1955 he was voted the George Woolf Memorial Jockey Award in recognition of his racing success accomplished with a high standard of personal and professional conduct, on and off the racetrack.
Ray York retired in 1992 having won 3,082 races. On January 13, 2000, the 66-year-old became the first jockey to ride in seven different decades when he rode a 4-year-old gelding named Culebra to a tenth-place finish in a seven-furlong claiming race at Santa Anita Park in Arcadia, California.