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Cheltenham’s Greatest: Five Of The Festival’s Most Exciting Moments

  • Written by Martina Maritato
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Every year the Cheltenham Festival produces incredible moments that live long in the memory. Few horse racing festivals can match it. We see history makers, underdogs upsetting the odds and more drama than an Eastenders double bill. But even so, there are a number of thrilling Cheltenham moments that stand above the rest. Horse racing fans up and down the country will be desperate for the 2019 Cheltenham Festival to produce more memories, but can they top these five moments from years gone by?


The Cheltenham Festival welcomes many high quality races over the festival, but it’s the Gold Cup they always grabs the headlines.

Over the years it’s made legends out of many horses, and Kauto Star ranks right up there with the very best.

The French-bred horse won the Gold Cup twice, in 2007 and 2009 becoming the first horse to regain the trophy after losing it in 2008.

A firm favourite in both races, Kauto Star’s dominance has been matched by very few, with the Paul Nicholls trained horse also winning four consecutive King George VI Chases and a record five in total.

He won his final Gold Cup by a staggering 13 lengths and is remembered as one of the very finest to this day.

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Arkle’s performances during the 1960s have comfortably marked the horse as perhaps the greatest steeplechaser in history.

Such was his power, he remains the Gold Cup’s shortest odds winner as he secured his third successive title in 1966.

That wasn’t without its tribulations though. In the 1966 Gold Cup, it didn’t look good for Arkle as he ploughed through a fence early in the race. He dug deep though, obliterating the field and going on to win by 30 lengths.

The Irish thoroughbred’s legend remains one of the most exciting in the sport and he remains as Timeform’s greatest ever, having picked up three Gold Cups, the King George VI Chase, the Irish Grand National and the Hennessy Gold Cup.


Nicky Henderson is a household name when it comes to the Cheltenham Festival, and it was long before the day that made him a true Festival legend.

While the likes of Mo Farah and Jessica Ennis’ incredible performances stole the sport headlines in 2012, Henderson managed to achieve a feat equally as impressive.

Like Super Saturday, the winners continued to tumble and along with them records as Henderson created history.

First up was Henderson’s 44th winner at the Festival  to title him as Cheltenham’s most successful ever trainer. The winners continued throughout the day, four in total, the most any trainer has achieved in one day.

By the end of Cheltenham he’d secured seven, the biggest haul in history and he’s still enjoying winners to this day.

They’ll be plenty of money going on his horses in the Cheltenham betting odds over the coming weeks and months, where he’ll undoubtedly build upon his legacy even further.

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1983 produced one of the most remarkable and memorable Gold Cup races in history. The race itself was won by Bregawn, a horse that had a series of great wins across 1982 and ‘83. But the race itself is perhaps more famous for the four horses that followed in behind.

Bregawn produced trainer Michael Dickinson’s last ever Gold Cup win, but that day he didn’t just secure a winner, he took the top five places in the Gold Cup.

It’s a feat that will likely never be replicated and a truly once-in-a-lifetime moment for all those stood in the crowd.


While 1989 was the year of the supreme Desert Orchid, 1990 produced the biggest shock in Cheltenham history.

Desert Orchid went into the race as favourite to win the Gold Cup at 10/11, but it was 100/1 shot Norton’s Coin which sent tremors across the horse racing landscape.

Not only did the nine-year-old upset the odds, he also ran six minutes 30 seconds, the fastest since 1953, to really make his mark.

Only Looks Like Trouble and Long Run have since run it faster, in what was a truly inspired race by Norton’s Coin and Graham McCourt.

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