Remembering Champion Horses who won The Gold Cup multiple times

February 23, 2021

The horses on this list have beguiled everyone from punters to the jockeys who rode them to victory repeatedly

The Gold Cup is one of the biggest national hunt races on the British and Irish race calendar, with grade 1 horses jumping the course’s 22 fences in search of glory.

Before looking ahead to the 2021 edition of this famous race, and its bumper £625,000 prize pot, we pay homage to the top eight horses who upset the odds and won the race twice or even thrice.

Al Boum Photo

With the next Cheltenham Festival due to take place from the 16th to the 19th of March, it only makes sense to kick this article off with the favourite for the Gold Cup. Al Boum Photo has won the cup for the past two years and will have no end of Cheltenham free bets being lumped on him for the third year in a row, by punters whose trust he has earned the hard way.

He had long odds when he first took down the biggest race at the festival in 2019, but has never looked back since, living up to the hype in 2020 and promising to do the same this time around.

If he can pull the feat off, he will not only make most betting punters thrilled but also join an exclusive club of horses to have ever claimed a hat-trick of Gold Cups in the post-war era. 

That club includes only two other legendary horses by the names of Arkle and Best Mate. It remains to be seen if Al Boum Photo will be every bettor’s best friend when he passes the winning post in March, but with offers like these for Cheltenham Festival, not too many horse racing fans should have much to moan about either way.

All that is left to do now is to sit back and see if Paul Townend can get things right in the saddle yet again, to send the grandstands into raptures.

Caption: The fences seen here don’t do justice to the monsters that horses and jockeys must tackle on the Gold Cup course

Kauto Star

Kauto Star was a force to be reckoned with between 2007 and 2009, writing himself into the history books by being the only horse ever to regain his Gold Cup title, having lost it against one-hit-wonder Denman in 2008.

That blip aside, this French horse went on to be regarded as one of the greatest chasers of all time, despite failing on many further attempts to regain his Gold Cup crown.


Whenever a conversation strikes up about which was the greatest steeplechaser in history, Arkle’s name is bound to pop up, and if it does not, then it is your duty to mention him.

He won the Gold Cup for three consecutive years from 1964 to 1966, his final win coinciding with England’s soccer World Cup victory, which perhaps makes English horse racing fans remember him even more fondly than they otherwise might have. 

Many a book has been written about the life and times of the famous horse, whose legend is still as strong today as it ever has been.

Best Mate

The only other horse to have won the Gold Cup three times is every punter’s Best Mate, having bagged the winning rosette from 2002 to 2004.

Unfortunately, Best Mate’s story was tarnished by his tragic passing at a race meet in Exeter, where a heart attack stopped him from fully enjoying the fruits of his success. However, by that time he had already captured the hearts of racing fans all over the world.

“For the best in horse racing, I read Past the Wire, and you should read it too.” Tommy Massis, Racehorse owner, Breeders’ Cup Betting Challenge Champion  

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