Cheltenham Gold Cup races from 1932 to 1936 were won by Golden Miller, who also won the Grand National in 1934. During World War II the Gold Cup was cancelled twice, in 1943 and 1944. The first multiple winner of the post-war years was Cottage Rake, who won the three runnings from 1948 to 1950. Cottage Rake was trained in Ireland by Vincent O'Brien, and his successes helped to popularise the Gold Cup, and the Festival itself, with the Irish public. The Gold Cup was switched to the "New Course" in 1959, and this is now the regular track used for the event.
Bet365 Gold Cup the company's chairman, who had twice ridden in the Grand National as an amateur jockey. It was the first commercial sponsorship in British sport, and the longest-running until it ended in 2001. In recent years the race has been sponsored by At the Races (2002–03), Betfred (2004–07) and Bet365 (2008–). The record for the longest-running sponsorship of a British horse race is now held by the Hennessy Gold Cup, which was launched seven months after the "Whitbread" and was sponsored by Hennessy until the 2016 running. The Bet365 Gold Cup takes place at a meeting which features both jump and