Cheltenham’s Gold Cup Heroes: Horses That Have Won Three or More Times

Cheltenham Racecourse crowds and race
Credit Sarah via Flickr

As the most prestigious race of the National Hunt season, the Cheltenham Gold Cup attracts the very best steeplechasers in the business. With so much elite competition tackling the three-mile, two-furlong test every March, it is an incredibly tough race to win. It is therefore a truly impressive feat when a horse records multiple victories in this contest.

These are the greats that feature most heavily in the folklore of the Cheltenham Gold Cup. The list below includes every horse who has won this race three or more times since it was founded, as a steeplechase, just over a century ago. This is the company current two-time champion Galopin Des Champs will join if he can secure another win in this year’s Gold Cup. He is well-fancied to do just that after his fine win in the Irish equivalent recently, that secured his hat-trick in that race. What a list of illustrious names he will join if he can successfully defend his crown again.

Golden Miller – 5 (1932, 1933, 1934, 1935, 1936)

Golden Miller
Credit Wikipedia

It seems only fair to start this list of Gold Cup heroes with the sole five-time champion, Golden Miller. The fact that no other horse has won this contest four times, let alone five, speaks volumes about just how good this horse really was. Although he is best remembered for his Gold Cup heroics, the Irish-bred horse also won the Grand National in 1934. Winning both premium steeplechase events is a feat only one other horse has ever managed.

Back to the Gold Cup, Golden Miller participated in some epic renewals. Some of them he made light work of but he faced a real battle in the 1935 edition. That year Golden Miller was accompanied by Thomond II as he cleared the final fence. The two battled deep to gain an advantage on the uphill run-in but the reigning champion simply had too much stamina and was eventually able to pull ahead.

If not for the English weather, Golden Miller may have earned himself six Gold Cup victories. Flooding meant organisers had to cancel the 1937 edition of the contest so he had to wait until 1938 for a sixth attempt. By this point, the ageing 12-year-old was past his peak and despite a valiant effort, he lost the lead on the run-in and had to settle for second. There is no guarantee he would have won a 1937 edition but given how good he looked in 1936 and how competitive he was two years later, he would have had a fantastic shot. Truly one of the very best of the best.

Cottage Rake – 3 (1948, 1949, 1950)

Failed by a vet on three separate occasions before he turned to steeplechasing, Cottage Rake almost did not have a career in the sport. Vincent O’Brien was unconcerned by the vet’s assessment though and believed he could still be a fine runner. And so he proved to be when winning the 1948 Gold Cup as a 10/1 shot before starting the next two years as the odds-on favourite. The first of them was a real battle as he was only able to shake off the challenge of Cool Customer right at the very end of the contest.

Arkle – 3 (1964, 1965, 1966)


While Arkle is inarguably one of the greats of the sport, he could have achieved even more if not for injury. After defeating reigning champion Mill House in the 1964 Gold Cup by an impressive five lengths, fully 25 lengths clear of third, the two faced a rematch in 1965. However, by this point, an increasingly commanding Arkle crushed Mill House by 20 lengths. As if this was not dominant enough, the following year the 1/10 favourite won by a yawning 30 lengths, the most emphatic win in Gold Cup history. Sadly Arkle injured himself while jumping at Kempton Park later in the year and never competed again.

Best Mate – 3 (2002, 2003, 2004)

Best Mate
Credit Chris Reynolds via Wikipedia

With no race in 2001, a busy field of 18 runners lined up seeking Gold Cup glory the following year. From them, it was Best Mate who prospered thanks to a solid jumping display. During his career, Best Mate never fell at a single fence or hurdle and it was this consistent jumping ability that served him so well in Cheltenham’s big race. He absolutely cruised to victory in 2003 but had to dig deep 12 months later as Sir Rembrandt pushed him all the way. He had his sights set on a fourth win in 2005 but the early 5-2 favourite pulled out days before the race after breaking a blood vessel.

Two Time Champions


Although it takes three wins to make it onto our Gold Cup heroes list, we wanted to quickly mention the few horses that won this race on two occasions. These include East Hero (1929, 1930), L’Escargot, who won in 1970 and 1971 and is the only other winner of this race and the National, Kauto Star (2007, 2009), Al Boum Photo (2019, 2020) and of course, Galopin Des Champs (2023, 2024). Can Galopin gallop one step closer to immortality and claim a third win very soon? Watch this space…