The 10 Biggest Upsets In Cheltenham Gold Cup History
The Cheltenham Gold Cup is widely regarded as the blue-riband race of the Cheltenham Festival, bringing together the finest staying chasers from Britain and Ireland each year.
Over the decades, the race has produced some legendary winners. Horses such as Desert Orchid, Kauto Star and Best Mate have all secured their place in racing folklore thanks to their Gold Cup triumphs.
However, the Festival showpiece has also delivered its fair share of major surprises since the race was first run in 1924.
With runners required to cover more than three miles and jump 22 demanding fences, the contest places a huge emphasis on stamina and jumping accuracy, which can open the door to unexpected results.
Below, we take a look at 10 of the biggest shocks in Cheltenham Gold Cup history - victories that stunned punters and delighted betting sites.
1. Norton’s Coin - 1990 - 100/1
Racing fans who watched the 1990 Gold Cup will never forget the remarkable victory of Norton’s Coin.
The Sirrell Griffiths-trained nine-year-old was sent off at 100/1, making him the biggest-priced winner in the race’s history.
Most of the crowd expected Desert Orchid, the 10/11 favourite and 1989 champion, to win again.
Instead, Norton’s Coin produced a stunning performance to land the prize, while the hugely popular "Dessie" could only finish third.
The shock result left Prestbury Park in disbelief.
2. Lord Windermere - 2014 - 20/1
Lord Windermere is not always the first name that springs to mind when discussing Gold Cup winners, yet his 20/1 success in 2014 remains one of the most memorable.
The eight-year-old lined up as a clear outsider, with Bobs Worth installed as the 6/4 favourite and plenty of support also behind Silviniaco Conti, Paul Nicholls' dual King George VI Chase winner.
However, under a perfectly judged ride from Davy Russell, Lord Windermere finished strongly up the hill to edge out On His Own in a thrilling finish.
3. Imperial Commander - 2010 - 7/1
At first glance, a 7/1 winner may not appear particularly shocking, but the context of the 2010 Gold Cup made Imperial Commander’s victory unexpected.
Much of the build-up focused on the rivalry between Kauto Star and Denman, who had dominated the previous three runnings of the race.
While attention was fixed on the famous stablemates, Imperial Commander, trained by Nigel Twiston-Davies, quietly produced a brilliant performance under Paddy Brennan.
Kauto Star fell late on, and Imperial Commander powered home to claim the biggest victory of his career.
4. L’Escargot - 1970 - 33/1
Despite his name translating to "The Snail", there was nothing slow about L’Escargot’s display in the 1970 Gold Cup.
The 33/1 outsider was largely overlooked before the race but showed tremendous stamina to secure victory for trainer Dan Moore.
He went on to confirm his class by winning the race again in 1971, and later achieved further fame by landing the 1975 Grand National, famously ending Red Rum’s streak of National victories.
5. Cool Ground - 1992 - 25/1
Just two years after Norton’s Coin stunned racing fans, another big-priced winner emerged.
Cool Ground, trained by Toby Balding, triumphed at 25/1 in the 1992 Gold Cup.
Much of the betting support centred on Carvill’s Hill, who started as the even-money favourite. However, the race didn’t go to plan for the market leader.
Cool Ground stayed on strongly to defeat The Fellow in an exciting finish up Cheltenham’s famous hill.
6. Cool Dawn - 1998 - 25/1
The Gold Cup has produced several memorable long-shot winners, and Cool Dawn’s 25/1 victory in 1998 is another example.
Trained by Robert Alner, he faced a competitive field of 17 runners, yet delivered an impressive performance to beat high-class rivals, including Dorans Pride and See More Business.
The victory marked one of the standout moments of Alner’s training career.
7. Mr Mulligan - 1997 - 20/1
Legendary jockey Tony McCoy enjoyed two Cheltenham Gold Cup victories, and the first came aboard Mr Mulligan in 1997.
Sent off at 20/1, the horse dominated the race and ultimately won by an emphatic nine lengths.
The race proved eventful, with several of the 14 runners failing to complete the course, including the 4/1 favourite Imperial Call.
Barton Bank, at 33/1, finished second.
8. Gay Donald - 1955 - 33/1
Only long-time racing followers are likely to remember Gay Donald’s Gold Cup victory in 1955, but it was another huge upset.
The 33/1 shot, trained by Tony Grantham, took control of the race early and built a commanding lead.
Neither the defending champion Four Ten nor other fancied runners such as Halloween were able to close the gap as Gay Donald held on for victory.
9. See More Business - 1999 - 16/1
While 16/1 might not seem enormous odds, it represented a surprise given the quality of the opposition in the 1999 Gold Cup.
See More Business, trained by Paul Nicholls, gave the future champion trainer his first Gold Cup victory.
Ridden by Mick Fitzgerald, the horse comfortably defeated Go Ballistic, who finished second at 66/1.
Meanwhile, favourite Florida Pearl finished a distant third, 18 lengths behind the winner.
10. Al Boum Photo - 2019 - 12/1
A 12/1 winner trained by Willie Mullins may not initially seem shocking, but Al Boum Photo’s victory in 2019 still surprised many punters.
The seven-year-old was not among the leading fancies beforehand, with Presenting Percy starting as the 10/3 favourite.
However, Al Boum Photo delivered a strong staying performance, defeating Anibale Fly by two and a half lengths.
The win was the first of back-to-back Gold Cup victories for the horse, who successfully defended his title in 2020.
Could There Be A Shock In The 2026 Gold Cup?
The 2026 Cheltenham Gold Cup looks wide open compared to some recent renewals, with several contenders towards the head of the betting.
Among the early favourites is Fact To File, who has developed into one of the leading staying chasers in training and is currently trading around 4/1.
Close behind in the market are The Jukebox Man, Jango Baie and Gaelic Warrior, all priced at roughly 11/2, suggesting bookmakers and betting apps view the race as highly competitive.
Other contenders attracting attention include defending champion Inothewayurthinkin, Grey Dawning and Spillane’s Tower, while I Am Maximus, the Grand National winner, also features among the entries.
With several closely matched runners near the top of the betting, the 2026 renewal could once again produce an unexpected winner - something the history of the Cheltenham Gold Cup shows is always possible.
* Odds correct at time of publication, 5pm, 06/03/26.
