Top Cheltenham Gold Cup Winners

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The Cheltenham Gold Cup is the climax of the Cheltenham Festival meeting and has been won by many of the greatest steeplechasers in history.

Opinions will vary as to the greatest of all time.

We have picked out our top ten Cheltenham Gold Cup winners, some for their sheer class and others for producing some memorable races.

Check out the Top 10 Cheltenham Gold Cup Winners:


Top Cheltenham Gold Cup Winners


Arkle is still the first name that springs to mind when discussing the greatest Cheltenham Gold Cup winners.

Timeform rated him at 212. To put that in perspective, that is 20lbs higher than Sprinter Sacre and 21lbs superior to Kauto Star.

He won the Gold Cup for three consecutive seasons from 1964 to 1966.

He is best remembered for his clashes with Mill House, particularly his 25 lengths victory in 1965.


Bregawn may not rank highly among the greatest Cheltenham winners but he will forever be associated with Michael Dickinson’s incredible 1983 Gold Cup.

Dickinson saddled the first five horses to finish; Bregawn, Captain John, Wayward Lad, Silver Buck and Ashley House.

Graham Bradley rode Bregawn and had him in front from the fifth fence, repelling his stable companions and bravely running on strongly to the line.

Burrough Hill Lad

Burrough Hill Lad was a big, dark brown gelding trained by Jenny Pitman.

He oozed class and burst onto the Gold Cup scene when cantering to victory in the Coral Welsh Grand National in 1983. He progressed the following season and was even more impressive when defying a big weight in the Hennessy Gold Cup.

He started 7-2 favourite for the Cheltenham Gold Cup in 1984 and beat Brown Chamberlin by three lengths.

Regular jockey John Francome was claimed for the runner-up with Phil Tuck stepping in for the winning ride.

Dawn Run

Dawn Run became the first (and only) horse in history to win both the Champion Hurdle and the Cheltenham Gold Cup.

The brilliant mare won the 1984 Champion Hurdle but her chasing career was interrupted by injury and mistakes.

In 1986 she unseated jockey Tony Mullins in her prep race and Jonjo O’Neill controversially stepped in for the Gold Cup ride. It must have been fate as Jonjo’s driving finish galvanised the mare to beat Wayward Lad and Forgive n’ Forget. It, along with the commentary of the BBC’s Sir Peter O’Sullevan, is one of the most memorable pieces of National Hunt racing ever recorded.

Desert Orchid

Desert Orchid was simply the people’s champion.

The bold jumping, front-running grey had a legion of supporters, earned through his sheer determination to win.

The fact that he was an attractive grey probably helped but he is one of very few racehorses to become a household name.

His victories include four King George VI Chases, an Irish National and a Whitbread Gold Cup.

Topping them all was his incredible Cheltenham Gold Cup win in 1989. The ground was bottomless and he looked to be floundering early in the straight as the mud-loving Yahoo was sent for home. To huge roars from the crowd, Simon Sherwood managed to get him going and he wore down Yahoo in one of the most thrilling horse races of all time.

Master Oats

Master Oats was trained by Kim Bailey and worked his way through the handicap system to emerge as the best chaser in Britain and Ireland.

He was officially rated 107 for a handicap chase at Uttoxeter in 1993 but it soon became clear he was a lot better than that. He beat Garrison Savannah, Young Hustler and Moorcroft Boy with embarrassing ease in the 1994 Greenall’s Gold Cup at Haydock.

The following season he defeated Earth Summit by 20 lengths in the Welsh Grand National, being slashed from 16-1 to 9-2 favourite for the Cheltenham Gold Cup.

Although he had his favoured soft ground, he did not jump well in the early stages and jockey Norman Williamson switched him out wide to get a better view of his fences. He went on to win by 15 lengths to add his name to the roll of honour.

Best Mate

Best Mate was another horse to capture the imagine of the public, completing a Gold Cup hat-trick from 2002 to 2004.

He was trained by Henrietta Knight and ridden by Jim Culloty and was prepared meticulously for Cheltenham each season.

His third victory was hard-earned as he battled past 20-1 shot Harbour Pilot before holding off the rallying 33-1 outsider Sir Rembrandt.

Best Mate won 14 of his 22 career starts including the 2002 King George VI Chase.

Kauto Star

Kauto Star, besides being a record five-time winner of the King George VI Chase, was also the first horse to regain the Cheltenham Gold Cup.

He was always a talented chaser but looked as though he might not stay three miles in his younger days.

His effortless victory in the Betfair Chase in 2006, the first of four in the race, ended those concerns and he automatically became Gold Cup favourite.

Although he made Kempton Park his second home, his second Gold Cup victory in 2009 was a notable achievement. He recaptured the crown from his stable companion Denman.


Denman always had the makings of a Gold Cup horse with trainer Paul Nicholls taking him through the tried and tested route of staying hurdles and the RSA Chase.

He was so imposing that he was dubbed “The Tank” and the horse that stood in his way for the Gold Cup was stable companion Kauto Star.

Ruby Walsh stuck with Kauto Star in the 2008 Gold Cup with Sam Thomas riding Denman. He won a memorable race by 7 lengths.

His other career wins included the Hennessy Gold Cup in 2007 and 2009, conceding lumps of weight to his rivals.

Al Boum Photo

Al Boum Photo ended the Cheltenham Gold Cup hoodoo for Willie Mullins, the leading trainer in the history of the festival meeting.

Mullins had finished second on six occasions prior to the 2019 Gold Cup and things did not appear to be going well in the early stages of the race. He had four representatives but Kemboy unseated rider at the first, Invitation Only fell at the tenth and Bellshill was pulled up. Meanwhile, Al Boum Photo was travelling cosily just behind the leaders and led on the home turn, going on to win by two and a half lengths.

Will Al Boum Photo back up his success and is it one of Willie Mullins’s Best Chances of a Cheltenham Festival winner this year?

He gained a second victory in 2020 but his hat-trick bid was foiled by the Henry De Bromhead trained Minella Indo and A Plus Tard.

Summary of Cheltenham Gold Cup Winners

The Cheltenham Gold Cup is the pinnacle of National Hunt racing and the ultimate prize.

The Gold Cup takes place on the final day of the Cheltenham Festival and many of the biggest horse racing tipsters love to select ante-post bets on the highest-profile chase race of the year hosted at the Cheltenham Racecourse at Prestbury Park.

As you can imagine, it has produced some amazing races and been won by the true legends of the sport.

If you think we have missed a great Cheltenham Gold Cup winner let us know and we will get them added.

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Please always gamble responsibly.

Subjects covered in our Cheltenham Gold Cup wins guide – Cheltenham Gold Cup champion, most successful horse, most successful trainer, Cheltenham racecourse, Cheltenham festival.