Before you read jockey Marcus Armytage’s feature on why the Cheltenham Gold Cup is still the pinnacle of jump racing, be sure to take a look at our guides to what to wear to the Festival for ladies and the gents.

The Cheltenham Gold Cup: the highlight of the jump racing season

When Red Splash, a five-year-old chestnut with a white blaze whose name only rarely crops up these days in pub quizzes, won the inaugural Cheltenham Gold Cup in 1924, few people could have guessed how big the race would go on to become. Back then it was all about the Grand National. Indeed that first Gold Cup, one of the few weight-forage non-handicap chases at the time, was very much regarded as a trial for Aintree, and the main talking point after that first running was less about Red Splash than Conjuror II’s head defeat in second that strengthened his position in the betting for Liverpool the following month.

As we approach the 100th anniversary of the race, the wheel has turned. Even though the National, a handicap dating back to 1839, has a longer history, tradition and is worth more, it finds itself somewhat under pressure. But partly because it is a handicap, the emphasis is on jumping and there are a lot of runners, the best horse does not always win. What’s more, crucial to the National’s charm, there is still something of the lucky lottery ticket about triumphing at Aintree in April. It is amazing how often it is won by a ‘good story’ rather than the obvious form horse.

In contrast, the Gold Cup is the pinnacle of the National Hunt season and jump racing in the British Isles. It is won by the best horse and has, for some time, been the race the professional’s professional would rather triumph in. “I’d say the Gold Cup is the one the pros prefer to win,” says Sir Anthony McCoy, who won it on Mr Mulligan in 1997 and Synchronised in 2012, although it was the 2010 National on Don’t Push It that won him BBC Sports Personality of the Year. “If you buy a horse, you’re aiming to buy a champion that can win the Gold Cup. You don’t really buy a horse to win a National; that’s often a byproduct of trying to buy a Gold Cup horse.”

Centenary celebrations for the Cheltenham Gold Cup

The only thing the Cheltenham Festival’s showpiece race has yet to achieve is the worldwide reach that comes with winning a National. However, in jump-racing circles at any rate, the Gold Cup is where the prestige is at. It was the brainchild of racecourse chairman Frederick Cathcart, who was commemorated in a race bearing his name until it was replaced by the Ryanair Chase. Back in 1924, though, the Gold Cup was not the main event at the Festival. That was the now 164-year-old, four-mile National Hunt Chase for amateur riders, which that year was twice as valuable at £1,285. The original Gold Cup, made for the 1924 race and now used as the perpetual trophy, has been housed in the Hall of Fame since it was returned to the racecourse in 2018. It is made from nine-carat gold and plated with 18-carat gold to give it its shine. 

Best Mate jumps the last with Jim Culloty on their way to win the Cheltenham Gold Cup, 14 March 2002 (GERRY PENNY/AFP via Getty Images)

As part of the centenary celebrations the Cup has travelled to all corners of Britain and Ireland. The man entrusted with taking it up Carrauntoohil mountain, the highest point in Ireland; Snowdon in Wales; Scafell Pike in England; and, obviously, Arkle in north-west Scotland; as well as an Albert Bartlett head office in Airdrie, Lucinda Russell’s stables in Kinross, and the London Horse Show is Cheltenham’s Andre Klein.

“The simple goal is to get the Cup out into the public,” he explains. “By allowing as many people as possible to be photographed with it, we can give them a personal affinity with the Gold Cup. At Ayr races on a Monday in December more than 1,000 people had their photos taken with it and a lot of stories came out. A chap who played football for Norton House in Glasgow at the time was telling me how he told all his mates to back Norton’s Coin, the 100/1 winner ridden by Graham McCourt in 1990. We are also promoting the book Let No Memories Fade about the race, compiled by Chris Pitt,” says Klein.

Legends of the Gold Cup

The 2024 race won’t actually be the 100th running of the Gold Cup. Frost did for it in 1931, it was waterlogged in 1937, while in 1943 and 1944 the Second World War stopped it and more recently, in 2001, it was called off because of foot and mouth. We cannot possibly mention all 81 individual winners of the race but no horse in modern racing currency has greater worth than Arkle, the three-time winner owned by Anne, Duchess of Westminster, named after the eponymous mountain on Grosvenor’s Reay Forest estate. He was trained by Tom Dreaper, ridden by Pat Taaffe and is immortalised by a life-size Emma McDermott bronze statue in Ashbourne, Co Meath near where he was trained.

Arkle, of course, is the beau idéal of chasers to which no horse has since come close to measuring, although Henrietta Knight’s Best Mate matched his three consecutive victories between 2002 and 2004 without being as invincible. But as every year passes since Best Mate’s wins, his reputation, and that of his trainer, is enhanced as people realise just how difficult a race it is to win three years in a row. No horse, however, has surpassed the achievements in the race of the extraordinary chaser Golden Miller, who won it five times in the 1930s. In a decade in which Phar Lap and Seabiscuit were earning legendary status on other continents, Dorothy Paget’s great chaser was doing the same here and his success was crucial in elevating the Gold Cup, still in its infancy then, in status and prestige.

So unpromising was Golden Miller’s racecourse debut that his trainer Basil Briscoe’s head lad, Stan Tidley, commented: “What a good name for a bad horse.” Remarkably, he was denied the chance of a sixth win when the race was abandoned, and a year later he was second, beaten two lengths by Morse Code after leading at the last. His wealthy owner, an American heiress, was somewhat of an eccentric. She slept during the day and woke at night when she would bet heavily on the previous afternoon’s racing, having struck a deal of trust with her bookmaker. After breaking down on the way to the races once, her Rolls-Royce was always followed to the races by another, sometimes two. Paget also hated men, which made her relationships with her trainers and jockeys – he was ridden by four different jockeys in his five wins – awkward, to say the least.

Golden Miller’s owner was an eccentric American heiress

My grandmother ‘Pug’ Whitehead, who trained and rode her showjumpers, recalls Fulke Walwyn sitting in one room, Paget sitting in another and acting as an intermediary between the two until the owner signed off with “And, while you’re about it, kick him in the balls from me.” Victory in 1932 did not win Golden Miller rave reviews mainly because Grakle, the odds-on favourite, was brought down when still going well. The year he won his third he went on to win the Grand National, becoming the only horse to complete the double in the same year, and by his fifth he had become the superstar horse of the inter-war years.

As much as I would like to dwell on the achievements of Kauto Star and his stablemate and adversary Denman, in terms of an actual horse race the best, most exciting Gold Cup I have witnessed was the one won by Desert Orchid in 1989. The general public had an affinity with the exuberant grey, trained by David Elsworth, who usually saved his best for Kempton on Boxing Day, where he won four King Georges. Cheltenham was not on his list of favourite places and even his owner, Richard Burridge, was disinclined to run on the desperately heavy ground, above which helicopters had been deployed to help dry. After the demise of Ten Plus three out, it became a duel between Dessie and the mud-lark Yahoo, who was running the race of his life.

Desert Orchid, one of racing’s best-loved horses, jumping a fence and going on to win the Cheltenham Gold Cup in 1989 (Picture: David Cannon/Allsport)

“Coming off the bend Yahoo was going very easily and, after jumping the second last OK, I thought Yahoo’s got this in the bag,” recalls Dessie’s jockey Simon Sherwood. “But between the last two fences Dessie changed legs and it was suddenly like going on good ground rather than bottomless. “We had to pop the last and landed in a heap but we had one chance and we had to forget the ‘knackeredness’. However, having lost momentum, about 10 strides after the last he suddenly started to pick up again and then started going left when, historically, he had always gone right,” continues Sherwood. “I had to correct him, otherwise we’d have put Yahoo into the Silver Ring. Afterwards it was all a bit surreal. I don’t think there have ever been many better receptions than that.” 

Cheltenham claims to fame

As an amateur rider, I only had eyes for Aintree and was never good enough to get a ride in the Gold Cup but I got engaged on Gold Cup day (Best Mate won it, so that narrows it down to one of three years – I’m not good with dates) and one of my claims to fame was winning the Plough Maiden Chase (Div II), worth £1,500 to the winner, at Southwell at Easter 1992 on Kim Bailey’s subsequent 1995 Gold Cup winner, Master Oats. There were still two horses in front of me turning into the straight but one fell and brought down the other, allowing Master Oats to get off the mark by beating the only two other horses to stand up.

Bailey loves telling the story of how I came back in and, on dismounting, said that he had done well to win with such a slow horse and that the Plough Maiden Chase might have been the pinnacle of the liver chestnut’s career. However, when he is recounting the tale he omits to say that he wholeheartedly agreed with me, which made us a pair of pretty rotten judges. I rode out Mr Mulligan as a young horse. He was so clumsy, tripping over a blade of grass and confirmed when he went a stride and tripped over his own feet at Newbury one day, that it never crossed my mind that he might be a Gold Cup winner. I also rode See More Business hunting with the Blackmore Vale in retirement but that is a long story. Suffice to say, it was also his last day’s hunting. One thing is for sure: whatever the name of this year’s Boodles Gold Cup winner, it will make more of a splash than the first.

If you enjoyed Marcus Armytage’s feature about the Cheltenham Gold Cup, be sure to read his article about how amateur jockeys made the Grand National the race it is today. And any budding race goers be sure to take a look at our guide to luxury country hats.