How many horses have won the Cheltenham Gold Cup more than once?

First run as a steeplechase just over a century ago, in 1924, the Cheltenham Gold Cup is the most prestigious and second-most valuable race of its kind run in Britain. The ‘Blue Riband’ event has been abandoned or cancelled a handful of times in its history but, in 96 runnings so far, has been won more than once by a total of nine different horses.

The first of them was Easter Hero, who justified favouritism in 1929 and 1930, winning by 20 lengths on both occasions. By that stage, he was owned by American John Jay Whitney, following the mysterious disappearance of his previous owner, Alfred Loewenstein, in 1928, and trained by Jack Anthony. The Cheltenham Gold Cup was abandoned due to flooding in 1931, but then followed the era of Golden Miller, who would win five years running between 1932 and 1936, not to mention the Grand National, too, in 1934, making him the only horse ever to win both premier steeplechases in the same season.

Following World War II, the legendary Vincent O’Brien saddled Cottage Rake to three successive wins in 1948, 1949 and 1950 and the latter was followed by the equally legendary Arkle, who did likewise in 1964, 1965 and 1966. L’Escargot, who famously denied Red Rum a hat-trick in the Grand National in 1975 had, by that stage, already won back-to renewals of the Cheltenham Gold Cup in 1970 and 1971. More recently, Best Mate won three times, in 2002, 2003 and 2004 and Kauto Star (2007, 2009), Al Boum Photo (2019, 2020) and Galopin Des Champs (2023, 2024) all won twice apiece.

Kauto Star

At the time of his retirement in October 2012, Paul Nicholls said of Kauto Star, “He’s definitely one of the greatest; it’s hard to compare generations, but in my lifetime he’s been the best and probably will be the best.” Over a decade later, Kauto Star remains the joint-fourth highest-rated steeplechaser since the early sixties, according to Timeform, alongside Mill House and behind only Arkle, Flyingbolt and Sprinter Sacre.

Owned by the late Clive Smith, who described him as a “a wonderful, wonderful horse and a good friend of mine”, Kauto Star won 23 of his 41 races over hurdles and fences and amassed over £2.375 million in prize money. He joined Paul Nicholls from Serge Foucher in France, as a four-year-old, in November 2004 and was immediately sent over fences. Kauto Star won his first Grade 1 race, the Tingle Creek Chase, over two miles, at Sandown Park in December 2005 and, having fallen at the third fence when favourite for the Queen Mother Champion Chase at the Cheltenham Festival in 2006, enjoyed arguably his best season ever in 2006/07.

That campaign, he was unbeaten in six races, including the Stayers Chase Triple Crown – the Betfair Chase at Haydock Park, the King George VI Chase at Kempton Park and the Cheltenham Gold Cup – and with it a £1 million bonus, as well as the Tingle Creek Chase for the second year running. He lost the Cheltenham Gold Cup to stable companion Denman in 2008, but regained it in 2009, reversing the previous from to the tune of 20 lengths and, thereby, became the first horse to do so. Away from the Cheltenham Festival, Kauto Star also won the King George VI Chase a record five times, in 2006, 2007, 2008, 2009 and 2011, his final triumph after retirement was mooted for the first time after he was pulled up, at odds-on, in the Punchestown Gold Cup the previous May.

Gerri Colombe

Owned by Robcour Racing, under the auspices of Irish multi-millionaire Brian Acheson, and trained by Gordon Elliott in Longwood, County Meath, Gerri Colombe is a nine-year-old gelding who has won 10 of his 14 races under Rules, including five Grade 1 steeplechases. By useful jumps sire Saddle Maker, from the family of Sadler’s Wells, out of a mare by Cadoudal, whose progeny include Big Buck’s and Long Run, he is certainly bred to be a steeplechaser.

Interestingly, though, for all his success elsewhere, Gerri Colombe has been to the Cheltenham Festival twice and has been beaten, although far from disgraced, twice. After winning his first three starts over fences, including the Faugheen Novice Chase at Limerick and the Scilly Isles Novices’ Chase at Sandown, he was sent off 5/4 favourite for the Broadway Novices’ Chase in 2023, but went down by a short-head to the aggressively ridden The Real Whacker. In 2024, he was sent off 13/2 second favourite for the Cheltenham Gold Cup, but had no answer to reigning champion Galopin Des Champs in the closing stages and was eventually beaten three and a half lengths.

Gerri Colombe resumed winning ways on his final start of 2023/24, when justifying favouritism in the William Hill Bowl Chase at Aintree, although only just, by half a length from Ahoy Senor, who was officially rated 12lb inferior. On his reappearance in 2024/25, he could finish only third of five, beaten 13½ lengths, behind Envoy Allen in the Ladbrokes Champion Chase at Down Royal, the first time he had finished outside the first two in his career. Of course, he may well have needed that race, but missed the Savills Chase at Leopardstown over Christmas after working poorly and, according to his trainer, could conceivably head straight to the Cheltenham Gold Cup without another run.

Rachael Blackmore

At the time of writing, Rachael Blackmore has only recently returned to the saddle, having recovered from a neck injury sustained in a fall at Downpatrick on September 20, 2024. Blackmore, 35, will always be best remembered as the first female jockey to win the Grand National, which she did on Minella Times, trained by Henry de Bromhead, in 2021, but has already rewritten the racing history books more than once in her pioneering career.

Born on July 11, 1989 in Killenaule, County Tipperary, Blackmore rode her first winner as a professional, Most Honourable, trained by John Joseph Hanlon, in handicap hurdle at Clonmel on September 3, 2015 and in the decade since has rarely looked back. In 2016/17, she became the first woman to win the Irish conditional jockeys’ title and rode out her claim on Sweet Home Chicago, trained by Colin Bowe, in a maiden hurdle at Wexford on June 21, 2017.

At the Cheltenham Festival, Blackmore rode her first winner, A Plus Tard, in the Centenary Novices’ Handicap Chase in 2019 and has since increased her career tally to 16 wins, notably including the Champion Hurdle, twice, on Honeysuckle (2021, 2022), the Cheltenham Gold Cup on A Plus Tard (2022) and the Queen Mother Champion Chase on Captain Guinness (2024).

Thus, she became the first woman to win each of those ‘feature’ races and, in 2021, when she rode a total of six winners, the first woman to win the leading jockey award at the Cheltenham Festival. The Stayers’ Hurdle is the notable omission from her CV, but she has also won the Ryanair Chase twice, on Allaho (2021) and Envoi Allen (2023). Remarkably, Blackmore is already sits in eleventh place on the all-time list at the Festival and, of jockeys still riding, only compatriot Paul Townend, with 34 winners, has achieved more success at the March showpiece meeting.

Fact To File

For readers unfamiliar with the name, Fact To File is an eight-year-old gelding, owned by John McManus and trained by Willie Mullins, who was briefly promoted to favouritism for the 2025 Cheltenham Gold Cup after beating the reigning champion Galopin Des Champs, also trained by Mullins, into third place in the John Durkan Memorial Punchestown Chase on November 24, 2024. However, when the pair met again in the Savills Chase at Leopardstown on December 28, 2024, Galopin Des Champs not only reversed the Punchestown form to the tune of ten and a quarter lengths, but did so emphatically, making all the running and drawing clear on the run-in to win going away.

Nevertheless, despite that reverse, at the time of writing Fact To File remains a top-priced 4.1 second favourite for the 2025 Cheltenham Gold Cup. The son of Poliglote, who has still had only six starts over regulation fences, was a ready, three-and-three-quarter-length winner of the Broadway Novices’ Chase, over three miles and half a furlong, at the 2024 Cheltenham Festival and is currently outright 4/1 favourite for the 2025 Ryanair Chase, back over the intermediate distance o two miles and four and a half furlongs.

Fact To File is currently rated 170+ by Timeform, 9lb inferior to Galopin Des Champs, with the inference that he may be better yet. For all that Willie Mullins has said that “Galopin Des Champs wouldn’t be seen at his best” over the two-and-a-half-mile trip in the John Durkan, McManus certainly has an embarrassment of riches in the staying chasing division, with the likes of Fact To File, Spillane’s Tower and Inothwayurthnkin at his disposal. Tony Mullins, brother of Willie, has already said of Fact To File, “…J.P. [McManus] has never owned one like this and he’s owned a lot of good horses”, so it will be fascinating to see what the future holds for the young pretender.

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