Cheltenham Festival Runners & Riders Racing Towards the Finish

Cheltenham Festival’s Best and Most Iconic Moments

Some of the best moments at Cheltenham Festival have become the most recognised in racing history. From Arkle’s legendary treble in the Gold Cup, to Big Buck’s successive World Hurdle four-timer and odds breaking horse races.

There’s much to celebrate looking back and even more to look forward to in the future as the Cheltenham Festival 2021 is full speed ahead.

Desert Orchid’s Cheltenham Gold Cup Win in 1989

The 1989 Cheltenham Gold Cup, won by Desert Orchid, will forever be a standout race and one of the best Cheltenham Festival moments. Desert Orchid was already a well celebrated figure, often regarded as the best two-miler of his era with a popularity that transcended across the globe.

He had missed out on the Gold Cup Chase the year before due to heavy grounds and 1989 offered no better turf. Thanks to a morning of snow and rain, the conditions were terrible but “Dessie” would still take his chance.

Coming up between the last two, Yahoo and Charter Party, a previous Gold Cup winner were the only horses alongside Desert Orchid still in contention for the race, with the rest of the field miserably behind.

As Dessie and Yahoo pulled away, it looked like the David Elsworth-trained horse was stuck in muddy ground as his rival edged further forward. But looks are deceiving because the famed grey horse stepped it up a gear, producing his signature attacking finish to hammer on home and take the title on Gold Cup Day.

The crowds were roaring both at Cheltenham Racecourse and behind TV screens for the popular figure.

Kauto Star Snatches the Gold Cup Title Back

After losing the title in 2008, Kauto Star came back with a vengeance in 2009 to regain the title from stablemate, Denman, nicknamed ‘The Tank’ who became a Cheltenham Festival Gold Cup winner after beating Kauto Star the year before.

It was an epic display under the backdrop of Cleeve Hills with both Paul Nicholls-trained horses fighting till the finish. In the end, Denman was no match for the 2007 winner, who, under the guidance of Ruby Walsh pulled away with three fences to go before unleashing a burst of speed and winning by 13 lengths.

The duo made making history look easy and Kauto Star was quickly recognised as a Cheltenham Festival icon, as he began being spoken about in the same manner as Arkle – immortal. He is the only horse in Cheltenham Festival history to regain a Cheltenham Gold Cup title.

This will definitely be remembered as one of, if not the best race of his career.

Michael Dickinson and the Famous Five in 1983

Sometimes referred to as the mad genius, Dickinson cemented his name in racing history by getting all his racehorses’ home in the first five positions during the 1983 Cheltenham Gold Cup Chase. It had never been seen before and will probably never be seen again – a true Cheltenham festival icon.

Kauto Star

Kauto Star being walked into Winners Enclosure

Bregawn led the pack which was made up of runners Silver Buck, Captain John, Wayward Lad and Ashley House. Readers of the Racing Post later voted Dickinson as having the greatest training performance in Britain. His commitment to his job and harvesting elite horses often left him exhausted.

Dickinson also became the first National Hunt trainer to take home more than £300,000 in a jumps race.

Arkle’s epic victory in 1966

Undoubtedly, one of the best moments at Cheltenham was Arkle’s 1966 victory. Arguably, all of Arkle’s Gold Cup wins were monumental but the third is often overlooked, perhaps because his biggest rival, Mill House was side-lined with a tendon injury. Yet the 1966 Gold Cup is probably the one he came closest to not winning.

In the early stages of the race he ploughed through a fence, giving the rest of a field an advantage and yet still crushed runner-up, Dormant, by 30 lengths to take the Cheltenham Gold Cup trophy.

Arkle, also referred to as ‘Himself’ became such a remarkable figure that Cheltenham, amongst other racecourses have dedicated a races in his honour.


Arkle - Cheltenham Gold Cup Winner

During the Cheltenham Festival, the Arkle Challenge Trophy takes place on Champion Day Tuesday, which is a Grade 1 race run over a distance of about 2 miles.

Norton’s Coin at 100/1 caused huge upset

One of the best Cheltenham Festival moments has to be Norton’s Coin’s win in 1990. At 100/1, he was perceived as a “candidate for last, not first” said trainer, Sirrell Griffiths on reflection.

Norton’s Coin wasn’t supposed to run in the Gold Cup but in a handicap race at the meeting. When Griffiths went to enter he realised he had missed the deadline for the chase and having no other option, entered the horse in the Cheltenham Gold Cup.

In the build-up, all attention was on Desert Orchid, who had returned to defend his title in the big race and it looked that he’d be victorious too – that was until the last three fences. Norton’s Coin defied all odds, edging closer to the front and under jockey, Graham McCourt, charged forwards to claim victory by three and a half lengths over second-place finisher, Toby Tobias. Bookmaker favourite, Dessie, trailed behind in third.

The 100/1 outsider also broke the course record that year – Cheltenham Festival icon? We think so.

Annie Power tumbles at final hurdle

Willie Mullins chased a four-timer on the opening day of the Cheltenham Festival five years ago, having achieved victory with Douvan, Un De Sceaux and Faugheen, all he needed was for 1/2 Mares Hurdle favourite, Annie Power, to take it home.

Bookmakers were facing an estimate pay-out of £50 million if Mullins-trained Annie Power took the trophy and it was looking that way too until the very last. She was four lengths ahead of her rivals, with no chance of them catching up until she clipped the top of the hurdle and crash landed, very badly.

It was a cruel end for any punters backing her but a much better day for the betting firms.

Annie Power recovered from the fall and won the Cheltenham Champion Hurdle a year later.

Sprinter Sacre stomped to glory after detrimental heart issues

The Nicky Henderson trained-Sprinter Sacre beat bookmaker favourite, Un De Sceaux to win the illustrious Queen Mother Champion Chase on Ladies Day at Cheltenham for a second time after retuning from severe health problems.

An irregular heartbeat had been detected in 2014 which had prevented Sprinter Sacre from having a go at back-to-back wins that year and in 2015. He had last entered the Queen Mother Champion Chase in 2013 where he won it by 19 lengths.

Top jockey, Nico de Boinville was in charge of steering the powerhouse, whom he did effortlessly and Henderson did a proper job of nursing him back to full health which Sprinter Sacre repaid him for.

Tearing away from the crowd, the infamous duo brought it home by seven lengths, cementing themselves as Cheltenham Festival icons.

Sprinter Sacre

Sprinter Sacre and jockey, Nico de Boinville

Racegoers weren’t shocked either, as the horse had quickly become a prominent figure in jumps racing and was worshipped by punters across the world.

Bryony Frost extends Ladies Day in 2019

Bryony Frost became the first female jockey to win a Grade One hurdle at the Cheltenham Festival last year with victory on Frodon in the Ryanair Chase.

She guided her charge to glory in what can only be labelled an extraordinary day and one of the most momentous in recent racing history. Women everywhere celebrated her success, which is definitely one of the best moments the Cheltenham Festival has produced and her career has continued to spike since.

Frodon had looked to be in trouble two out but he didn’t give up and on releasing the reserved fuel in the tank, the pair soon pulled away. Frost likened the horse to Pegasus, stating “he has wings.”

Cheltenham has created fairy tale moments for all; jockeys, trainers and racegoers. The Festival attracts the world’s best horses and with results often being created in dramatic fashion, there is plenty to celebrate at Cheltenham Racecourse.

Click here to learn more about Cheltenham’s first races, winners and how the Ireland v England Cheltenham rivalry began.

Who, in 2021 will write their tale in racing folklore as a Cheltenham Festival Winner?

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