Tags: Jockey (Horse Racer).
Charles Charlie Cunningham (1849-1906) was a 19th-century Scottish National Hunt jockey who has been described as Scotland’s greatest jockey.Although he was an amateur throughout his career he won the Scottish Grand National a record four times (1881 1885 1887 and 1889) and also the National Hunt Chase Challenge Cup in 1886. He is also one of only two jump jockeys to ride six winners in one day a feat he achieved at Rugby Hunt on 29 March 1881.