Cheltenham the Biggest wins and Upsets

For punters and bookmakers alike, Cheltenham can bring elation or heartbreak. The history of the Festival is littered with big wins, heartbreaking near-misses and devastating losses. It has also thrown up its share of surprise winners in the big races too.


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At the 2017 Festival, an unnamed punter from south London picked up £251,382.34 from a £1 bet. The 67-year-old factory worker had backed five horses each-way with a Lucky 31 at Ladbrokes, with four of them winning. However, the story could have had an even happier ending — had his fifth selection Dodging Bullets come in, he would have walked away with more than £1 million.

2016 also saw another punter take away a huge win on the first day of the Festival. Steve Spinks, from Clacton in Essex, bet £2 on a 7-fold acca with Betdaq, with all seven selections coming in. Ruby Walsh rode three of the winners — Douvan, Annie Power and Vroum Vroum Mag — with the other winning legs being Altior, Un Temps Pour Tout, Minella Rocco and Ballyalton.

Another record-breaking win was recorded at the 2008 Festival when a punter in Scotland won £199,562 from a £300 bet when he backed the first four winners on the first day. His acca, which he placed with William Hill in Kilmarnock, included Katchit in the Champion Hurdle which came in at 10-1.

Perhaps the biggest success story of all came in 2012 when Conor Murphy, a stable lad with champion trainer Nicky Henderson, won £1 million on a 5-fold acca. What made the win even more special was that one of the winning legs, Finian’s Rainbow in the Queen Mother Champion Chase, was a horse that Murphy himself rode in track work every day.

Interestingly, the payout was so large because Murphy put his bet on some four months before the Festival — had he done so on the Monday before it began, his winnings would have been a much more modest £32,050.

The Cheltenham Festival has produced its share of devastating loss stories as well. In 2017, it was reported that a punter lost £500,000 in a single bet on course when odds-on favorite Douvan performed well below par and was pulled up in the Queen Mother Champion Chase, which was won by Special Tiara. However, the unnamed punter’s woes were perhaps not as bad as they might have been, considering he reportedly landed a £400,000 win the day before when Altior saluted in the Arkle Challenge Trophy.

As well as honoring its champions, Cheltenham loves an underdog too. There have been plenty of shock winners at the Festival over the years that no punter could have realistically expected to be on.

Perhaps the most famous of these was the 1990 Gold Cup winner Norton’s Coin. 100/1 on the day of the race, which featured the country’s most beloved horse and the reigning champion Desert Orchid, Norton’s Coin was trained by small-time trainer Sirrel Griffiths, whose day job was as a dairy farmer. Ridden by Graham McCourt, Norton’s Coin held on to win by just under a length from Toby Tobias, wth ‘Dessie’ coming in third.

Although Hardy Eustace was a two-time winner of the Champion Hurdle and widely regarded as one of the best hurdlers of his generation, his first victory in the feature race in 2004 came out of the blue. Under the guidance of Dessie Hughes and ridden by Conor O’Dwyer, at 33-1 Hardy Eustace was given little chance before the off, especially as the 2003 winner and hot favourite Rooster Booster was in the field. However, O’Dwyer and Hardy Eustace jumped out in front and were never headed, and this shock win proved to be the first major victory of an emerging champion.

In 2007, Ebaziyan was another surprise Festival winner, taking out the Supreme Novices’ Hurdle at 40-1. Although he had some reasonable form behind him on the flat and had won a maiden hurdle, not a lot was expected of the Willie Mullins-trained grey. However, with Davy Condon aboard, he never looked troubled despite the much-fancied Granit Jack and Amaretto Rose being in the field, and in the end had a relatively comfortable three-length win.