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  • A Brief History Of The Cheltenham Gold Cup, Its Best Horses, Trainers And Jockeys

A brief history of the Cheltenham Gold Cup, its best horses, trainers and jockeys

With the possible exception of the Grand National, the Cheltenham Gold Cup is the most coveted prize in jump racing. Planet Sport discovers why.

Commentating on perhaps the most famous Gold Cup of all time, the late, great Sir Peter O'Sullevan said: "Now they're rounding the home turn. And this is it! And Willie Robinson's got his whip out. And Pat Taaffe is shaking up Arkle."

And yes, this really is IT. It's the Cheltenham Gold Cup, the ultimate test for horse and rider over regulation fences. Three-and-a-quarter miles around the unforgiving Prestbury Park circuit. All geldings carrying the same weight, while mares have a 7lb sex allowance.

This is the crème de la crème of National Hunt racing and year on year a champion is crowned.

Cheltenham Gold Cup early years

Inaugurated in 1924, in its infancy the Gold Cup was a great race to win, but the Grand National still very much held sway as the premier jumps race on the planet.

History recalls that on 12 March 1924, nine runners went to post for the race, with the five-year-old Red Splash coming home in front under jockey Dick Rees, for trainer Fred Withington.

Easter Hero became the first dual winner of the race, justifying favouritism in both 1929 and 1930.

Golden Miller

With no race in 1931 due to frost, by the time the horses returned for the 1932 renewal, a star was born.
Golden Miller, owned by the wealthy eccentric Dorothy Paget, won the first of an astonishing five successive Gold Cups, under four different jockeys. He remains the only horse ever to have won both the Gold Cup and the Grand National in the same year (1934).
Unquestionably, his string of successes put the race very firmly on the map and the desire to win it was heightened.

Cottage Rake

Ballinode had become the first Irish-trained winner as early as 1925, but the Emerald Isle had to wait until after World War II for a second success through Prince Regent.
His trainer Tom Dreaper remains on the list of all-time greats, through his later handling of Arkle, but before that it would be Vincent O'Brien who stole the headlines for Ireland.
O'Brien went on to be arguably the greatest trainer of racehorses on the Flat, but prior to that he ruled the world of National Hunt and the horse that made his name was Cottage Rake. He won three successive Gold Cups from 1948-50, all under jockey Aubrey Brabazon.
O'Brien added a fourth Gold Cup success to his CV when sending out Knock Hard to win in 1953.


The 1960s was a vintage era for the Cheltenham Gold Cup. Standing out like a beacon were the performances of the great Arkle, who won the race in three successive years (1964, '65 and '66). He barely broke sweat in the latter two years, but the 1964 race, as referred to earlier, remains one of the classic jump races ever run.
Fulke Walwyn had trained the outstanding Mandarin to win the 1962 renewal and a year later, he sent out Mill House, a giant of a horse, to win the blue riband.
The six-year-old dominated his 11 opponents to such an extent that he was thought unbeatable and the best English-trained horse since Golden Miller, if not better.
Later that year, Mill House and Arkle met for the first time, in the Hennessy Gold Cup at Newbury. Carrying 5lb more than Arkle, Mill House put up a scintillating display of jumping to beat the Irish challenger. After that, no Brit would hear of defeat if they met off level weights in the Cheltenham Gold Cup the following March.
So good was the pair that only two other horses turned up on that March day in 1964, Pas Seul, who had won the Gold Cup in 1960, and King's Nephew. Neither got a look-in, as the big two dominated the contest, drawing clear down the hill on the second circuit.

As they rounded the home turn, Pat Taaffe let out a little rein on Arkle, who came from just off the pace set by Mill House and Willie Robinson, jumped the last upsides, and cleared away up the hill to win by seven lengths. The English were devastated.

"This is the champion. This is the best we've seen for a long time", said Peter O'Sullevan on commentary. He was right, as for the next three years, Arkle rewrote the rules of National Hunt racing, such was his dominance.

It also says something about the quality of Mill House that, after injury forced the end of Arkle's career, 'the big horse' was still good enough to win the 1967 Whitbread Gold Cup at Sandown, one of the most prestigious races on the calendar.
Taaffe and Dreaper also combined to win a further Gold Cup in 1968, with Fort Leney.

The 1970s

The 1970s dawned with another Irish-trained back-to-back winner in L'Escargot.

Trained by Dan Moore and ridden by Tommy Carberry, L'Escargot would arguably go on to become more famous for his two Grand National clashes with the great Red Rum, finishing second to him in 1974 and exacting his Aintree revenge a year later.

Throughout most of the '70s Britain's two top trainers remained Fred Rimell and Fred Winter, with Peter Easterby nosing them out as the decade came to an end.

That Rimell-Winter rivalry naturally took in the Gold Cup. Rimell, who'd won it in 1967 with Woodland Venture, did so again in 1976 with Royal Frolic.

Winter, meanwhile, finally landed a prize he'd twice won as a jockey, as the handler of 1978 winner Midnight Court.

Winter had some of the 1970s' major chasing stars that didn't manage to win the Gold Cup. Perhaps most famously, Pendil succumbed to his arch rival The Dikler on the run up the hill to the post in 1973. 

Then, a year later, when odds-on and apparently cruising, Pendil was brought down four fences from home by faller High Ken. As he told Planet Sport's Jonathan Doidge, jockey Richard Pitman blamed himself.

Captain Christy was hailed as the best since Arkle when he got the better of The Dikler in a tight finish to that 1974 renewal, and Easterby got his name on the trophy when Alverton, partnered by Jonjo O'Neill, emerged from the snow to land the last Gold Cup of the decade.

Michael Dickinson and the 'Famous Five'

Easterby won a second Gold Cup with Little Owl in 1981, before fellow northern-based trainer Michael Dickinson enjoyed domination like we have never seen before or since.
In 1982, Dickinson followed what Easterby had done in '81 by training the first two home, Silver Buck and Bregawn. Then in 1983, incredibly, the master of Dunkeswick saddled the first five home in the race.
For the record, the winner was Bregawn, chased home by stable companions Captain John, Wayward Lad, Silver Buck and Ashley House. It was phenomenal feat of training and a record that has thus far proved impossible to surpass.
As the '80s moved into full swing the Gold Cup became no less exciting. Burrough Hill Lad was an outstanding performer beset by injury, but his trainer Jenny Pitman became the first woman to train a Gold Cup winner when she got him there in prime condition in 1984.
The roof was raised in 1986, when Dawn Run became the first (and remains the only) horse to complete the Gold Cup-Champion Hurdle 'double', having won the latter race two years earlier. The mare carried Jonjo O'Neill to success on both occasions.
The decade certainly went out with a bang because in 1989, the people's champion Desert Orchid finally overcame his Cheltenham hoodoo to win in conditions that were barely raceable. In doing so, under Simon Sherwood, he confirmed himself to be one of the all-time greats.

100/1 winner kicks off the 1990s

However, that hoodoo struck again for 'Dessie' in 1990. Having looked head and shoulders above the rest and on ground that should have been much more suitable for him, he went off a short-priced favourite but was beaten by Norton's Coin.

The Cheltenham crowd was dumbstruck and looking at their racecards as Graham McCourt drove the 100/1 shot up the hill to win it for Welsh dairy farmer Sirrel Griffiths, with Desert Orchid third.

One of the tightest finishes to the race came in 1994, when The Fellow just got the better of the previous year's winner Jodami, so becoming the first French-trained winner of the race.

Mr Mulligan provided a pre-Sir Anthony McCoy with his first win in the race in 1997, while See More Business saw out the 20th Century with a first success in the race for trainer Paul Nicholls.

Best Mate

The 21st Century was ushered in with a win for future multiple champion jockey Richard Johnson on Looks Like Trouble.
After foot and mouth meant that no Festival was possible in 2001, we witnessed the only horse since Arkle to win three successive Gold Cups, Best Mate.

Prepared meticulously from her Oxfordshire base by Henrietta Knight, Best Mate won the 2002, 2004 and 2004 renewals.

Although there were some expressions of disappointment that he didn't run more often, there is no doubt that 'Matey', who ran in the claret and blue colours of Aston Villa fan Jim Lewis, was the best of his generation.

Kauto Star and Denman

As the 2000s drew to a close, a rivalry emerged to challenge even that of Arkle and Mill House over 40 years earlier.
Living in boxes side-by-side at the Ditcheat stables of Paul Nicholls, the pair were to meet several times on the racecourse. Born just two days apart, Denman being the older, their only competitive meetings were at Cheltenham.
Like many French-breds, Kauto Star was a little more forward than his stablemate and while Denman was winning the 2007 RSA Chase, the championship for novices, Kauto Star was winning his first Gold Cup.

Four the four years that followed, the pair faced-off at Prestbury Park. Denman had shouldered topweight to win the 2007 Hennessy Gold Cup, to announce himself as a Cheltenham contender, but Kauto Star was sent off as favourite on 14 March, 2008 as the tape went up for the Gold Cup.

Dominating the race from the halfway point, Denman and Sam Thomas had the field well strung out as they turned for home, and ground it out up the hill to knock his stablemate off his perch with a wonderful seven-length success. The win earned Denman the nickname 'The Tank'.
One day short of a year later they were at it again. In the 12-months in between, Denman had been diagnosed as having an irregular heartbeat and there was a real chance that he may not race again. Nicholls was patient with him and reported in the final few days before the Gold Cup that he was coming back to being something like his best.
Kauto Star, meanwhile, was still rated number one on the back of two more Grade 1 successes on route to the 2009 Gold Cup, when he cemented that position with a 13-length demolition of 'The Tank', whose effort had been commendable given what he had ailed. With that victory, Kauto Star became the first (and remains the only) horse to regain the Cheltenham crown.
Both horses competed in two more Gold Cups, Denman getting the better of his stablemate both times but winning neither. He finished second to Imperial Commander in 2010 and in the same spot behind Long Run in a vintage renewal in 2011, in which Kauto Star finished third.

Recent Irish dominance

If those were halcyon days for both the Brits and the race itself, it is Ireland that has dominated more recently.

After Bobs Worth earned Nicky Henderson a second win in 2013 (he'd also trained Long Run), six of the last eight winners have been prepared in Ireland.

Lord Windermere sprang a 20/1 surprise in 2014, making Jim Culloty the latest person to have both ridden and trained a Gold Cup winner.

Don Cossack gave Gordon Elliott his only Gold Cup success to date when he won the 2016 version, while Jessica Harrington (Sizing John, 2017), Willie Mullins (Al Boum Photo, 2019 and 2020) and Henry de Bromhead (Minella Indo, 2021) have added further names from the Emerald Isle to the trainers' roll of honour.

And amid all of that, Native River won west country farmer-turned-trainer Colin Tizzard got the better of Might Bite in 2018, getting one back for Britain in one of the most thrilling renewals of the race.

Did you know? Cheltenham Gold Cup facts

  • The first recorded running for a 'Cheltenham Gold Cup' took place in July 1819 and was a Flat race contested on Cleeve Hill, overlooking the current racecourse site. The three-mile contest was won by Spectre.
  • A prize of £685 went to the owner of Red Splash, the first winner of the Gold Cup as we now know it, in 1924. In 2022, the winning owner will receive £351, 688.
  • The 1937 race was abandoned due to flooding.
  • There was no Gold Cup in 1934 and 1944 due to World War II.
  • The 1957 winner Linwell was trained by esteemed journalist Ivor Herbert (see 'The Winter Kings') who was unable to be named as trainer because he was not allowed to hold a training licence.
  • The 1980 winner, Tied Cottage, was subsequently disqualified after a banned substance was traced in his urine.
  • The race was first sponsored in 1972 by Piper Champagne. In 2022, Boodles will sponsor the race for the first time.
  • Tom Dreaper has trained the winner most times, five in total.
  • In addition to her five wins with Golden Miller, Dorothy Paget also owned 1940 winner Roman Hackle and 1952 winner Mont Tremblant. She remains the winning-most owner with seven.

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