Prestbury Park, Cheltenham

The 4 Biggest Upsets in Cheltenham Festival History

The Cheltenham Festival is known to many as the ‘World Cup of Jumps Racing’, bringing together the world’s finest steeplechasers and hurdlers at Prestbury Park.

With such a strong field of entrants in each of the 28 races throughout the four-day festival, it’s no surprise that the pre-race favourites don’t always get things their own way.

In fact, there have been some major upsets through the years at Cheltenham Festival, which this article will delve into in greater detail. These examples of shock victories are a reminder of what can happen and that no Cheltenham bet is a sure-fire thing.

Surprises and upsets

There are tipsters with years, if not decades, of experience in punting at Cheltenham. Many of whom spend weeks, if not months, crunching the data and understanding the types of horses and attributes needed to win certain races at the festival. The likes of Tony Calvin and Kevin Blake have already published their Cheltenham tips 2023 Festival articles, which cover every event on the festival’s four daily racecards with qualified selections.

To whet your appetite for the potential surprises that may lurk at the 2023 Cheltenham Festival, here are four of the biggest surprise results in the event’s 163-year history.

Norton’s Coin – 1990, Gold Cup

Norton’s Coin is considered by many to be the biggest Cheltenham Festival upset yet. It just so happened to occur in the festival’s most prestigious race, the Cheltenham Gold Cup. Norton’s Coin was a 100/1 outsider for the 1990 Gold Cup. Despite being a winner of the South Wales Showers Mira Silver Trophy Chase at the previous festival, Norton’s Coin was still unfancied.

In many ways, the warning signs were there. Norton’s Coin had run a creditable second in Cheltenham’s Lechlade Handicap Chase. Nevertheless, finishing ahead of the iconic Desert Orchid was by no means in the script. Jockey, Graham McCourt, took Norton’s Coin for the ride of his life, pipping Toby Tobias to a Gold Cup triumph by half-a-length.

Kirriemuir – 1965, Champion Hurdle

Although this upset was 58 years ago, it is no less surprising talking about it all these years on. Kirriemuir was handed odds of 50/1 in the Champion Hurdle. It was the biggest odds ever given to an entrant in the Champion Hurdle.

The bookies were right to do so on paper, given that Kirriemuir was up against the likes of Hatton’s Grace and National Spirit. Trainer, Fulke Walwyn, was even at a loss to explain Kirriemuir’s stunning victory.

Observer Corps – 1989, Cathcart Challenge Cup

Observer Corps was entered into the Cathcart Challenge Cup at the 1989 festival, having been off the track for 11 months. Prior to this, the eight-year-old hadn’t even come close to landing a win in any of his four previous races.

Trainer, John Edwards, didn’t raise any eyebrows at the bookmakers’ 66/1 price for his charge for the Cathcart. Edwards will have raised more than his eyebrows after watching Observer Corps power to a comfortable victory by eight lengths.

Ebaziyan – 2007, Supreme Novices’ Hurdle

The Supreme Novices’ Hurdle is the first race of the entire festival. As the curtain-raiser, there is a lot of excitement and intrigue about the Supreme Novices’ Hurdle. It’s often a great race for future talent spotting too. All-time greats like Altior and Vautour have prevailed in this race at past festivals.

The Willie Mullins-trained Ebaziyan didn’t look like troubling the leaders in 2007. The indifferent form of three wins in eight races meant that Ebaziyan never stood out on paper, resulting in him being priced as a 40/1 outsider. Sure enough, Ebaziyan would demonstrate serious pace to outfox pre-race favourite, Amaretto Rose, to clinch the win. Ironically, Ebaziyan would only win two more races in his career.

Have we missed any Cheltenham Festival upsets that are etched in your memory? Let us know in the comments section!

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