Ranked: The 10 Biggest Upsets in Cheltenham Gold Cup History

Ranked: The 10 Biggest Upsets in Cheltenham Gold Cup History
© PA
Graham McCourt aboard Norton's Coin, the 100/1 winner of the 1990 Cheltenham Gold Cup

The Cheltenham Gold Cup is the blue riband race of the Cheltenham Festival, with the best chasing horses in the UK and Ireland competing every year to land the spoils.

We’ve seen some brilliant Gold Cup-winning horses over the past few years, with Desert Orchid, Kauto Star and Best Mate among those winners who have taken their place in the Hall of Fame.



However, there have also been some shocks in this showcase race since it was first ran in 1924. The fact that the runners have to travel a distance over three miles and encounter twenty-two fences means it can be a stamina-sapping contest, while there are inevitably horses that either fall or have to be pulled up along the way.

In this article, we look at the ten biggest upsets in the Cheltenham Gold Cup and they would have all given bookmakers a cause for celebration. It goes to show that anything can happen in the race and that it doesn’t always pay to follow the favourites!

  1. Norton’s Coin, 1990, Odds 100/1

  2. If you’re aged forty or older, the chances are that you will remember the 1990 Gold Cup where the unfancied Norton’s Coin pulled off an almighty shock in front of a packed crowd. Most of them had expected 10/11 favourite Desert Orchid to follow up that 1989 victory, although the Sirrel Griffiths-trained horse ran the proverbial blinder.

    At odds of 100/1, the nine-year-old was the biggest priced winner of this race, with the popular “Dessie” only able to finish third and it’s fair to say that there was a stunned silence around Prestbury Park that day.

  3. Lord Windermere, 2014, Odds 20/1

  4. Lord Windermere would probably be a Pointless answer when it comes to naming Gold Cup winners despite his recent triumph. The eight-year-old was regarded as nothing more than an outsider when lining up in the 2014 Gold Cup renewal, with Bobs Worth trading as 6/4 favourite and there was also money for two-time King George winner Silviniaco Conti.

    However, Davy Russell was able to steer the Irish horse to victory after an exciting race up the hill against 16/1 shot On His Own, with the pair proving to have the better stamina on the day.

  5. Imperial Commander, 2010, Odds 7/1

  6. You might not think that a 7/1 winner of a Cheltenham Gold Cup could resemble a shock, although the Nigel Twiston-Davies horse wasn’t supposed to be part of the media narrative which was pitching stablemates Kauto Star and Denman against each other for this showdown.

    After all, the pair had collectively won the previous three renewals, although it was their younger adversary who was steered home by Paddy Brennan, with Kauto Star unfortunately falling late in this eleven-runner race.

  7. L’Escargot, 1970, Odds 33/1

  8. L’Escargot literally translates as “The Snail” although there was nothing slow about this horse’s performance in the 1970 Cheltenham Gold Cup, with the rank outsider being completely unfancied in the lead up to this race and there was little to suggest he would be a contender.

    However, the Dan Moore-trained charge illustrated stamina in abundance and would go on to retain his Gold Cup crown in 1971, while the horse would go on to win the 1975 Grand National and halt Red Rum’s winning run in the process.

  9. Cool Ground, 1992, Odds 25/1

  10. Two years after Norton’s Coin landed that shock success in the Gold Cup, there was another big-priced winner of the race, with Cool Ground winning for trainer Toby Balding at a big price. Carvill’s Hill was all the rage leading up to the off and was sent off as the even money favourite.

    However, the Martin Pipe-trained horse was seemingly distracted by Golden Freeze throughout the race and Cool Ground was able to fend off 7/2 shot The Fellow in an exciting finish up that famous hill.

  11. Cool Down, 1998, Odds 25/1

  12. Cheltenham Gold Cup history is littered with big priced winners and Cool Dawn became the latest to triumph in 1998 when managing to finish first in a relatively large field of seventeen runners.

    Robert Alner wasn’t particularly well known, although it was a superb training performance that saw the horse beat rivals such as Dorans Pride and See More Business.

  13. Mr Mulligan, 1997, Odds 20/1

  14. Tony McCoy enjoyed two victories in the Cheltenham Gold Cup and the first came on Mr Mulligan, with the 20-time champion jockey steering the horse to an impressive nine-length victory over his rivals.

    As is often the case, several of the fourteen runners failed to complete the course including 4/1 favourite Imperial Call, with Barton Bank also running a blinder at 33/1 to finish second.

  15. Gay Donald, 1955, 33/1

  16. Only horse racing enthusiasts of advancing years will remember Gay Donald obliging in the 1955 Gold Cup at odds of 33/1, with Tony Grantham saddling the winner of this race for the only time.

    1954 winner Four Ten had been the confident shout before the off and there was also money for Halloween, although Gay Donald built up a sizeable early lead and the chasing pack weren’t able to reel him in.

  17. See More Business, 1999, 16/1

  18. The good thing about the Cheltenham Gold Cup is that you can back a perfectly good horse at 16/1 considering the high calibre of the other runners in the race. That certainly applied to 1999 winner See More Business, with Paul Nicholls saddling his first victor in this race.

    Go Ballistic was in second place and would have provided a much bigger shock at 66/1, with favourite Florida Pearl finishing a full eighteen lengths behind the eventual winner who was ridden by Mick Fitzgerald.

  19. Al Boum Photo, 2019, 12/1

  20. A 12/1 Gold Cup winner trained by Willie Mullins might not technically rank as a shock, although the seven-year-old was well down the betting order for this race, with Presenting Percy trading as the 10/3 favourite, although he could only manage eighth place.

    Clan Des Obeaux and Native River also failed to last the distance and it was the Grand National-contending Anibale Fly who gave the eventual winner the most to think about before Al Boum Photo won by two and a half lengths.

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