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For aficianados of National Hunt racing, the Cheltenham Gold Cup represents the pinnacle of the sport and for any owner, jockey or trainer, winning the ‘Blue Riband’ event is a dream come true. However, in just over a century since the Cheltenham Gold Cup was established, as a steeplechase, in 1924, a select few men have managed to win the race as a jockey and as a trainer.

Fred Winter, for example, won back-to-back renewals of the Cheltenham Gold Cup on Saffron Tartan and Mandarin in 1961 and 1962 and, following his retirement from the saddle in 1964, later saddled Midnight Court, ridden by John Francome, to victory in 1978. Likewise, Pat Taaffe won the Cheltenham Gold Cup as a jockey, three times on the incomparable Arkle, in 1964, 1965 and 1996 and again on stable companion Fort Leney in 1968, also won as a trainer with Captain Christy in 1974.

The last person to achieve the notable double, though, was Killarney-born James ‘Jim’ Culloty who, as a jockey, completed in a hat-trick in the Cheltenham Gold Cup on Best Mate, trained by Henrietta Knight, in 2002, 2003 and 2004. Having retired from the saddle in 2005, he subsequently trained Lord Windermere, ridden by Davy Russell, to win a dramatic renewal in 2014. In so doing, he became just the fourth man, after Danny Morgan (who achieved the feat back in 1959), Winter and Taaffe to ride and train a Cheltenham Gold Cup winner.

The Cheltenham Festival is, of course, the flagship week in British National Hunt racing and, since 2005, has been a four-day extravanganza, nowadays featuring 28 quintessential races across every discipline of the sport. Half of those races are Grade 1 races, in which horses compete off level weights, subject to allowances for age and gender, but at least one of the so-called ‘feature’ races forms the highlight of each day.

Traditionally, the four feature races are the Champion Hurdle, Queen Mother Champion Chase, Stayers’ Hurdle and Cheltenham Gold Cup, but it would be fair to say that the Festival Trophy, or Ryanair Chase, which was introduced in 2005 and promoted to Grade 1 status in 2008, now rivals the Stayers’ Hurdle for top billing on the third day of the Cheltenham Festival.

The oldest, most valuable and, by far, most prestigious of the quintet is the Cheltenham Gold Cup, run over three miles and two and a half furlongs on the New Course on the final day. Nowadays worth £625,000 in prize money, the race has been won by some of the finest steeplechasers in history. Second billing goes to the two-mile hurdling championship, the Champion Hurdle, which was established just three years after the Cheltenham Gold Cup, in 1927, and is run on the Old Course on the opening day. Arguably slightly further down the pecking order come the two-mile chasing championship, the Queen Mother Champion Chase, the three-mile hurdling championship, the Stayers’ Hurdle, and the aforementioned Ryanair Chase, which is run over the ‘intermediate’ distance of two miles and four and a half furlongs.

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.