How many horses have won the Cheltenham Gold Cup more than once?
First run as a steeplechase just over a century ago, in 1924, the Cheltenham Gold Cup is the most prestigious and second-most valuable race of its kind run in Britain. The ‘Blue Riband’ event has been abandoned or cancelled a handful of times in its history but, in 96 runnings so far, has been won more than once by a total of nine different horses.
The first of them was Easter Hero, who justified favouritism in 1929 and 1930, winning by 20 lengths on both occasions. By that stage, he was owned by American John Jay Whitney, following the mysterious disappearance of his previous owner, Alfred Loewenstein, in 1928, and trained by Jack Anthony. The Cheltenham Gold Cup was abandoned due to flooding in 1931, but then followed the era of Golden Miller, who would win five years running between 1932 and 1936, not to mention the Grand National, too, in 1934, making him the only horse ever to win both premier steeplechases in the same season.
Following World War II, the legendary Vincent O’Brien saddled Cottage Rake to three successive wins in 1948, 1949 and 1950 and the latter was followed by the equally legendary Arkle, who did likewise in 1964, 1965 and 1966. L’Escargot, who famously denied Red Rum a hat-trick in the Grand National in 1975 had, by that stage, already won back-to renewals of the Cheltenham Gold Cup in 1970 and 1971. More recently, Best Mate won three times, in 2002, 2003 and 2004 and Kauto Star (2007, 2009), Al Boum Photo (2019, 2020) and Galopin Des Champs (2023, 2024) all won twice apiece.