On Saint Paddy’s Day Friday 17th March, the world’s best steeplechasers will line up to contest the world’s most prestigious jumps race – the Cheltenham Gold Cup. For fans of jump racing all over the world, this is the race; the absolute pinnacle of the National Hunt calendar.

Few moments in sport can match the excitement of this early spring afternoon in the glorious setting of Prestbury Park in the Cotswold Hills. Through the years, the great race has brought fans of the sport some incredible moments. The grueling 3 miles, 2½ furlongs with its stamina-sapping undulations and uphill finish means no horse and its connections can even think about counting their chickens until the winning post has been passed. This toughest of run-ins has meant heartbreak for some of the greatest steeplechasers in history who just couldn’t quite cut it at Cheltenham – and glory for others who proved they had the heart for this race of all races.

The greatest of them all was five-times on the bounce winner of the 1930s, the legendary Golden Miller. Aged just five when he won his first Gold Cup in 1932, he would undoubtedly have started favourite for a sixth straight win in the 1937 race – but it was cancelled due to snow. What’s more, the Miller also won the Grand National in 1934, an unbelievable feat which remains unique.

Sadly, there are few people alive today who can remember Golden Miller’s unbelievable victories – so setting this great horse aside if we may, here are five of the Gold Cup’s most memorable moments from a list that seems endless…

5. L’Escargot’s 1970 win

L’Escargot remains the only other horse to emulate Golden Miller’s feat in winning both the Grand National and Cheltenham Gold Cup – albeit in separate years in L’Escargot’s case.

L’Escargot won back-to-back Gold Cups in 1970 and 1971 – adding the Grand National four years later when he dethroned then dual winner Red Rum (though “Rummy” was giving 11lbs to the two-time Gold Cup winner). He was owned by the U.S. Ambassador to Ireland, Raymond Guest, a former polo player, who wanted to name his horse “Let’s Go” – but the name was already taken so he went for the similar sounding L’Escargot. French for “the snail”, it was to prove highly inappropriate. 

For the 1970 race, L’Escargot was a 33/1 outsider in the Cheltenham odds. But as they came up the famous Cheltenham hill he was positively eating up the ground. As they turned for home and headed to the second last, he jumped alongside 8-1 chance French Tan who took the fence better and went on by a length. But L’Escargot rallied and they jumped the last together. Again, French Tan jumped the fence far better and momentarily looked like winning. But L’Escargot was surely one of the gutsiest horses ever to come under rules – and he gradually got stronger on the run-in under the guidance of the great Tommy Carberry to win by 1½ lengths.

He followed up the following year with the field well-strung out behind him and the bookies a lot wiser to the heart he had for Cheltenham – as a 7/2 winner.

4. Desert Orchid’s 1989 triumph

Desert Orchid was probably the most popular jumper since Red Rum. But whereas Red Rum was a household name – Desert Orchid was more of a racing fans’ favourite. In the late 80s-early 90s, the horse described as a grey, but who was actually near white in colour, showed unbelievable heart in landing the 3-mile King George VI Chase at Kempton Park four times; first in 1986, when an unfancied 7-year old, and again in 88, 89 & 90 (he was runner-up in 1987 to big outsider Nupsala).

But the biggest prize of them all, the Gold Cup, was considered to be beyond him due to the harder course, additional distance – and Dessie’s tendency to jump to the right (Kempton being a right-handed course, unlike Cheltenham).

As his debut in the race approached in 1989, rain and snow in the days before steadily made the going heavy – conditions which didn’t suit the horse. But trainer David Elsworth persuaded the owners to let Dessie have a crack at the race anyway. The weather had played into the hands of the mud-loving Yahoo who glided past Dessie after the third last and looked all over the winner as they jumped the penultimate fence.

As they approached the last, brave Dessie began to rally under hard driving from jockey Simon Sherwood, but still Yahoo took it better and appeared to be going away on the run-in. Yet Desert Orchid’s courage was what endeared him so much to racing fans – and the 1989 Gold Cup run-in epitomised this bravery perhaps more so than any other moment in racing’s rich history. The mighty roar of the 58,000-strong Cheltenham crowd seemed to pull Dessie back into the reckoning as he drifted left but still made up the ground. As they crossed the line, the seemingly impossible had happened and Dessie had won by one and a half lengths through sheer determination – bringing the house down as he did so.

After the race, Simon Sherwood said: “I’ve never known a horse so brave. He hated every step of the way in the ground and dug as deep as he could possibly go”. “Three cheers” were called for Dessie in the winners’ enclosure – and chanted heartily by his many thousands of fans.

The 1989 Gold Cup was subsequently voted “best horse race ever” by readers of the Racing Post; it’s not hard to see why – and all the credit goes to this most loved of all horses since Red Rum himself.

3. Best Mate’s 2004 win

In 2004, the Henrietta Knight-trained Best Mate became the first horse since the legendary Arkle to win three Gold Cups – an achievement bettered only by Golden Miller and equalled by Cottage Rake in 1948, 49 & 50. But in the modern era, it was widely believed within racing that such a feat was probably impossible.

Of his three Gold Cup triumphs, the 2004 event was not only his crowning glory, but by far the most exciting race. For the 2002 race, the 7-year old was sent off a 7-1 shot, and was cruising in third round the final turn under Jim Culloty behind See More Business and Commanche Court before quickening away approaching the last – and going on to win by 1¾ lengths. The following year, he won by a street, well within himself, and going away from the field on the run-in.

But on the day of the race in 2004, the ground was much softer than the great horse liked and connections had real doubts. Nevertheless, he was sent off at odds-on; the shortest price of any of his three wins.

Best Mate travelled well throughout the race, and his jumping was exemplary. Three fences from home, he looked poised but as they approached the second last, he became completely boxed in against the rail by Paul Carberry on Harbour Pilot and Andrew Thornton riding the outsider Sir Rembrandt. But Jim Culloty kept his cool, steered Best Mate wide and jumped the penultimate fence in fine style – to a deafening roar from the appreciative Prestbury Park crowd. He jumped the last half a length clear of Harbour Pilot and began to go clear, but Sir Rembrandt came with a blistering run on the outside and almost managed to overturn the great Best Mate – who turned out the half-length winner, much to the Cheltenham faithful’s relief. A couple more strides and Sir Rembrandt, a 25-1 chance, would surely have pegged him back.

This third win didn’t see Best Mate at his most sublime – but it certainly saw him at his most dogged and courageous – and it’s that that makes this his greatest moment; true grit.

The following year, Best Mate had to be withdrawn from the Gold Cup a week before the race having burst a blood vessel. Then in November 2005, he collapsed and died of a suspected heart attack having been pulled up by Paul Carberry when racing at Exeter. His death made national headline news. The most successful Cheltenham Gold Cup horse of the modern era was cremated and his ashes are buried next to the Cheltenham winning post – a fitting tribute to an amazing racehorse.

2. Kauto Star regains the throne in 2009

Ask any National Hunt aficionado who the greatest horse since Arkle was and you’ll probably get “Kauto Star” in reply. His record from a career that lasted almost eight years is simply unbelievable.

He remains the only horse to have won the King George VI Chase on four consecutive occasions – beginning in 2006. He then added a fifth in 2011 having been found to be suffering from an infection and having bled during the 2010 race won by Long Run.

He started the 2007 Gold Cup as hot favourite at 5/4 and won comfortably despite making a hash of the last fence to give his legions of fans a few palpitations.

The following year, despite being sent off 10/11 favourite, he never really seemed to settle into the race, jumping unevenly throughout. He went down by seven lengths to stablemate Denman, but still showed his battling qualities by staying on doggedly despite being out of sorts.

But it was his performance in the 2009 race that was to deservedly cement his place in racing history – pulling off a feat that has never been matched before or since. Quite simply, Kauto Star was imperious on the day. His jumping display was faultless and by three from home, he was clearly going to win comfortably barring disaster. He went on to win by a comfortable 13 lengths from his great rival Denman and in so doing achieved what 24 horses had unsuccessfully attempted to do on 34 separate occasions previously – in regaining the ultimate jumping accolade. The performance was described by Timeform as: “Arguably the best performance in the race since Arkle” and deservedly so. If his runs in previous Gold Cups had been all about heart – this was sheer class.

1. Arkle’s 1966 “World Cup” win for Ireland

Arkle is officially the greatest steeplechaser of all time with a Timeform rating of 212. But those who remember the greatest ever don’t need statistics to confirm what they could see with their own eyes through the burgeoning medium of television in the mid-1960s.

When he first came to prominence, however, it seemed like the reigning Gold Cup champion and also one of the highest rated horses ever, Mill House, had his measure. When the two first locked horns in the 1963 Hennessy Gold Cup, Mill House won whilst giving Arkle 5 lbs.

But in the following year’s Gold Cup, Arkle upset the odds by beating 8/13 favourite Mill House by five lengths at odds of 7/4. This was the last time the legend wouldn’t start as favourite for any race. In 1965, Arkle’s greatness had already made him a household name amongst the public – even those not particularly interested in racing.  This year, he won his second Gold Cup beating Mill House by 20 lengths in doing so – and at odds of just 3/10 which reflected his dominance.

The following year, in what was to be England’s World Cup winning year at football, Arkle proved himself king of the world for the Emerald Isle. He was the shortest-priced favourite ever in the race, being sent off at just 1/10. But at the end of the first circuit, “Himself” as he came to be known ploughed straight through a fence giving his followers a heart-stopping moment. Nevertheless, he went on to win his third consecutive Gold Cup at a canter by 30 lengths in what was surely the most emphatic victory in the great race by the greatest horse to have graced the Cheltenham turf.

Later that year, in the King George VI, Arkle hit guard rail jumping an open ditch, fracturing a pedal bone in the process and was never to run again.

“Himself” was once described by the late Sir Peter O’Sullevan as a freak of nature. His 1966 victory may not be the most emotive of Cheltenham Gold Cup moments; that honour surely goes to Desert Orchid in 1989, but it was surely the most dominant – from a horse who was simply the best.

A footnote if we may; the above great moments are unfair for all those great Gold Cup moments we haven’t mentioned. Chief among them is perhaps Dawn Run’s courageous 1986 win when the mare became the first, and so far only, horse ever to have won a Champion Hurdle (which she did in 1983) and a Gold Cup.