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.
Gordon Elliott (racehorse trainer) first winner at the Cheltenham Festival as a trainer was Chicago Grey in the prestigious National Hunt Chase Challenge Cup in 2011. He won the 2016 Cheltenham Gold Cup for the first time with Don Cossack. In the 2017 Cheltenham Festival he finished as the top trainer for the first time with six wins. It was the same number of wins as Willie Mullins but Elliott had one more second place than Mullins. In the 2017 Grand National Elliott trained Cause of Causes which came second. Elliott finished the 2016/17 season in second place to Mullins in the Irish national