The Cheltenham Festival is just about the biggest event in all of horse racing, and within that, the Gold Cup stands as the most important single race. It’s everyone’s dream to land a winner in the day four showpiece at Prestbury Park, from the jockeys and trainers taking part to the punters who bet on Cheltenham races with BetOnline.

Over the years, we’ve seen plenty of drama in the Gold Cup, from long-odds winners to dramatic finales. However, some have stood a level above in terms of how well they’ve performed in the Gold Cup on numerous occasions. Let’s have a look at those who have made the blue riband contest their own.


We have to go all the way back to the 1930s to find the most successful horse in the history of the Gold Cup. Indeed, he had quite an apt name. Golden Miller won the race on five consecutive occasions between 1932 and 1936, a remarkable run of form that saw four different jockeys and two trainers benefit from the horse’s supreme talents.

A couple of horses have won the Gold Cup in three successive years. The most famous of these is Arkle, who enjoyed his trio of wins in the 1960s, but don’t forget about Cottage Rake, who achieved the same feat between 1948 and 1950.

More recent examples of Gold Cup dominance include Best Mate’s memorable trio of wins in the early 2000s, and Al Boum Photo’s recent double in 2019 and 2020. 


It’ll be no surprise for many that Pat Taaffe is the leading jockey in the Cheltenham Gold Cup roll of honor. The Irishman is famous for being the man in the saddle of Arkle, a legend of racing who has a race named after him in the modern version of the Cheltenham Festival. Taaffe deserves his place in the history books as well, having produced some outstanding performances in the saddle to earn four Gold Cup wins in total.

Jim Culloty deserves a special mention for his three successive wins on board Best Mate, and the Irishman is a rare example of someone who has won the Gold Cup as both a jockey and a trainer, with Lord Windermere succeeding in 2014.


Tom Dreaper is a name you’ll see cropping up a lot in the Cheltenham Festival history books, and it is he who boasted the most Gold Cup winners throughout his career. As the trainer of Arkle, it’s no surprise to see him high up the list, but he also boasted two other wins — his maiden Gold Cup title with Prince Regent in 1946, along with Fort Leney’s win in 1968. Dreaper will forever be remembered as one of the Festival’s leading lights.

Since we talked about Golden Miller earlier, it’s worth mentioning Basil Briscoe’s efforts in saddling the famous Gold Cup winner on four consecutive occasions. Fulke Walwyn, Vincent O’Brien and Paul Nicholls have four winners to each of their names — an impressive achievement to say the least. Meanwhile, Owen Anthony and Henrietta Knight have both earned three Gold Cup winners.