Horse Racing

Five of the Biggest Upset Wins at the Cheltenham Festival

Biggest Upset Wins at the Cheltenham Festival

The 2025 Cheltenham Festival is almost upon us and at NetBet, we can give you the very best horse racing odds at our betting site for some of the meeting’s biggest races.

With that in mind, we take a look back at some of the Festival’s biggest ever shocks. Not necessarily the biggest prices, but those horses who may have stunned the racing world over the biggest four days in the calendar.

Read on to find out more!

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Norton’s Coin – 100/1 (1990 Cheltenham Gold Cup)

We start with arguably the biggest shock ever, let alone at just the Cheltenham Festival. The unfancied Norton’s Coin reigned supreme in racing’s Blue Riband, the Cheltenham Gold Cup, putting Welsh dairy farmer, Sirrell Griffiths, in the spotlight. Griffiths had a handful of horses he trained and quietly fancied his charge to run well at the Festival. Rivals included odds-on favourite, Desert Orchid, who won in 1989 and Toby Tobias. As the race reached a crescendo, “Dessie” and Toby Tobias were challenged by Norton’s Coin, ridden by Graham McCourt, at the final fence. The outsider surged clear up the famous hill amid a stunned silence from the crowd. To this day, Norton’s Coin remains the biggest-priced winner of the Gold Cup in history. Could there be another seismic shock on the cards this year?

Lisnagar Oscar – 50/1 (2020 World Hurdle)

Trained by Rebecca Curtis, Lisnagar Oscar had some decent bits of form heading into the 2020 renewal of the World Hurdle, but very few expected him to come out on top in a titanic battle at the finish. Having been beaten comfortably by the much-fancied Paisley Park in his previous run at Cheltenham, Lisnagar Oscar battled with Ronald Pump at the end of the gruelling three-mile contest to nose in front at the line, with Paisley Park a distant seventh. Lisnagar Oscar was much more popular with punters in the 2021 edition but fell at the seventh flight when in contention. 

Cue Card – 40/1 (2010 Champion Bumper)

Cue Card is a horse synonymous with the Festival. Having run during the four-day extravaganza on numerous occasions, the first time proved to be his most surprising success. Having won on his debut in a small race at Fontwell, Cue Card turned up to the Festival a somewhat unfancied 40/1 chance for Colin and Joe Tizzard. However, as the race unfolded, Cue Card waltzed through the field and annihilated some top-class horses, including Al Ferof. Cue Card then became something of an equine celebrity at the next few Festivals, but had little to no luck in most of his races, falling twice late on in two editions of the Gold Cup when still bang in contention. A legendary Cheltenham horse, but even the best can still be unfancied!

Azertyuiop 15/8 (2004 Queen Mother Champion Chase)

In the grand scheme of things, Azertyuiop is by no means the biggest-priced winner in this list. But his victory here saw fans of the legendary Moscow Flyer with their heads in their hands after the Irish challenger clouted the fourth-last fence and fell, to groans from the capacity crowd. Azertyuiop, ridden by Ruby Walsh, was billed as Moscow Flyer’s closest challenger but not many thought the young pretender to the crown could topple the Irish horse. As it turned out, these two would do battle in many more races and Moscow Flyer got his revenge in the 2005 renewal when Azertyuiop made a terrible mistake at the water jump, effectively ending his race.

Cool Dawn 25/1 (1998 Cheltenham Gold Cup)

Definitely an unheralded winner, Cool Dawn entered Cheltenham folklore 27 years ago when making all the running to win the 1998 Gold Cup under a superb ride from Andrew Thornton. Starting at odds of 25/1, Cool Dawn had the fancied runners and riders off the bridle from a long way out. Coming round the home turn, only Strong Promise and Dorans Pride were able to live with the furious gallop that Cool Dawn had set. Strong Promise threw down the gauntlet coming up the hill but the winner battled on bravely to secure a famous triumph for Thornton and trainer, Robert Alner.

 

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