Skelton started as an apprentice jockey aged 13, and rode his first winner (a dead heat) aged 15 at Wingatui. He was the leading apprentice in New Zealand for four consecutive years, and champion jockey seven times, and was outside the top four of the premiership between 1947 and 1979 only four times. He rode a record 124 winners in the 1967–68 season, and in May 1980 became the first New Zealand jockey to ride 2000 winners; he finished with 2179. He remains the most successful jockey of the 20th century in New Zealand with those figures. According to Skelton, the best horse he rode was
Daryl's Joy, champion New Zealand two-year-old in 1968, champion three-year-old in Australia in 1969, and later successful in the United States. Skelton won both the
W. S. Cox Plate and the
Victoria Derby on
Daryl's Joy in Australia. The big two-mile victories in New Zealand included the
Auckland Cup on Lucky Son, which he also trained; his father-in-law Fred Pratt's mare Foglia D'Oro in the
New Zealand Cup; and Loofah and Noir Filou in the
Wellington Cup. ==Honours and awards==