Cheltenham Gold Cup

Cheltenham Festival 2021: Six of the best Gold Cup winners

The Cheltenham Festival is the main event on the horse racing calendar. Four days of top-class racing at Prestbury Park, hundreds of thousands of racegoers (usually) coming through the turnstiles, and the finest horses in the world going head-to-head in some of the sport’s biggest races.

Of course, the highlight of the week comes on Friday in the shape of the Cheltenham Gold Cup. We’ve taken a look at some of the greatest horses in Cheltenham Festival history in recent weeks and you can check out our Champion Chase, Champion Hurdle and Stayers’ Hurdle blogs in our horse racing section. But now for our greatest Gold Cup winners – here are six of the very, very best:

Golden Miller

The most successful Gold Cup horse ever. The first running of the Gold Cup was in 1924, but it was in 1932 when the Cheltenham Festival struck gold. Never has there been a more appropriately named horse than Golden Miller, a five-time winner who won the first of SEVEN Gold Cups in 1932 for owner Dorothy Paget.

He was just five then, but age was no barrier, going on to follow up in the four years after. It was in 1934 where greatness was confirmed – he remains the first and only horse to win the Gold Cup and the Grand National in the same year. Golden indeed.


Golden Miller may have been the most successful Gold Cup horse ever, but Arkle was the best. This superstar still has the highest Timeform rating (212) of any horse ever and brought huge success to his owner, Anne Grosvenor, the Duchess of Westminster, during the 1960s. No relation to us!

Success includes three consecutive Cheltenham Gold Cups and a whole host of other top race win under the guidance of jockey Pat Taaffe. And his legacy remains – the Arkle Chase is one of the most exciting races of Cheltenham Festival week.


While Golden Miller is the only horse to do the Gold Cup and Grand National double in one year, one other horse has done both and that horse is L’Escargot – most famous for denying Red Rum a third successive Grand National win as a 12-year-old in 1975.

Rewind five years and there was still nothing snail-like about him, racing to Gold Cup successes in both 1970 and 1971. L’Escargot was a 33/1 winner in the former, which remains the joint longest-priced winner in Gold Cup history. Trained by Dan Moore and ridden by Tommy Carberry, the duo made it two 12 months later.

Best Mate

We’ve had the most successful and the most gifted. Now for arguably the most-loved horse in the history of Cheltenham and UK racing in general. Best Mate was a Cheltenham Gold Cup winner in 2002, 2003 and 2004.

We’ll never know if he would have made it four in a row – a burst blood vessel a week before the 2005 Festival denied him the opportunity. His tragic death at Exeter later that year made front page news, but he’ll forever be a part of Cheltenham history – his ashes are buried beside the winning post.

Kauto Star

The only horse to regain the Cheltenham Gold Cup, Kauto Star won the race in 2007, justifying favouritism for Ruby Walsh and Paul Nicholls. That success completed the Stayers’ Chase Triple Crown and earned connections a £1M bonus!

Stablemate Denman got the better of Kauto Star in 2008, but the roles were reversed in 2009 with a brilliant performance, racing clear by seven lengths and creating another little piece of history.

Al Boum Photo

The reigning champion, the back-to-back champion, the back-for-more champion. Al Boum Photo was a popular winner in 2018, giving Wille Mullins a long-awaited first Gold Cup success after 19 years of trying.

At 12/1, he was the longest-priced winner since Lord Windermere in 2014 – and went off at 100/30 when Paul Townend repeated the success 12 months ago, fending off Santini by a neck in a thriller.

Al Boum Photo looks to join the exclusive three-in-a-row club in 2021 and is a 5/2 favourite in the Cheltenham Gold Cup betting – take a look at the latest odds with Grosvenor Sport.

*Stated odds correct at time of writing

For more horse racing betting and Cheltenham Festival ante-post odds, make your way to Grosvenor Sport and get set for the biggest week in horse racing.

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