The jockey who holds the record for the highest number of Cheltenham Festival winners in a single year is Rupert ‘Ruby’ Walsh. Walsh retired from the saddle on May 1, 2019, just two weeks shy of his fortieth birthday but, by the end of his career, had ridden a total of 59 Cheltenham Festival winners and become leading jockey at the Festival on 11 occasions between 2004 and 2017. Walsh rode his first Cheltenham Festival winner on Alexander Banquet in the Champion Bumper, as an 18-year-old amateur, in 1998 but, as a professional, rode seven winners over the four days of the Festival not once, but twice.
His first record-breaking haul came in 2009, when his notable winners included Master Minded in the Queen Mother Champion Chase, Big Buck’s in the World Hurdle, now the Stayers’ Hurdle, and Kauto Star in the Cheltenham Gold Cup, all for Paul Nicholls. Of course, Walsh and Nicholls parted company in 2013, with Walsh choosing to concentrate on riding for Irish champion trainer Willie Mullins. However, the end of one of the most successful partnerships in the history of National Hunt racing did Walsh little harm as far as the Cheltenham Festival was concerned. Indeed, in 2016, Walsh equalled his own record by riding seven winners, all trained by Mullins, at the Festival. Notable winners that year included Douvan in the Arkle Challenge Trophy, Annie Power in the Champion Hurdle and the ill-fated Vautour in the Ryanair Chase.
For the uninitiated, Arkle was arguably the greatest steeplechaser of all time. In a four-year period between 1962 and 1966, Arkle won 22 of his 26 races over fences – including the Cheltenham Gold Cup three years running in 1964, 1965 and 1966 – and finished behind just six horses. His Timeform Annual Rating, of 212, is the highest ever awarded to a steeplechaser and 20lb superior to any other steeplechaser in history, with the exception of his stable companion, Flyingbolt. Arkle was owned by Anne Grosvenor, Duchess of Westminster, and trained by Thomas William ‘Tom’ Dreaper at the family farm in Greenogue, Kilsallaghan, Co. Dublin, Ireland.
The Cheltenham Gold Cup was inaugurated, as a steeplechase, in 1924 but, in the best part of a century, just four amateur jockeys have won what has become the most iillustrious prize in the British National Hunt calendar. Hugh Grosvenor did so on Thrown In in 1927, as did Richard Black on Fortina in 1947 but, since the Cheltenham Gold Cup was transferred to the New Course at Prestbury Park in 1959, just two other amateur jockeys have been led into the hallowed winners’ enclosure after the ‘Blue Riband’ event.
In 1981, Jim Wilson rode the seven-year-old Little Owl, trained by Peter Easterby, to a 1½-length victory over stablemate Night Nurse, thereby preventing him from becoming the first horse to complete the Champion Hurdle – Cheltenham Gold Cup double. Exactly three decades later, in 2011, Sam Waley-Cohen won a highly competitive renewal of the Cheltenham Gold Cup on the six-year-old Long Run, owned by his father, Robert, and trained by Nicky Henderson. Despite facing the three previous Cheltenham Gold Cup winners, in the form of Denman, Kauto Star and Imperial Commander, Long Run was sent off 7/2 favourite after comfortably winning the King George VI Chase at Kempton. The market support was justified; Long Run took the lead at the final fence and stayed on strongly to beat Kauto Star by 7 lengths, with Denman 4 lengths further beind in third place.
The Champion Hurdle and the Cheltenham Gold Cup represent the pinnacle of achievement in their respective divisions of National Hunt racing so, unsurprisingly, jockeys who have managed to win both races in the same season are few and far between. Norman Williamson did so in 1995, courtesy of Alderbrook and Master Oats, respectively, both trained by Kim Bailey.
However, the last jockey to complete the Champion Hurdle – Cheltenham Gold Cup double was Sir Anthony McCoy, popularly known as A.P. McCoy or Tony McCoy. On March 11, 1997, McCoy rode the six-year-old Make A Stand, trained by Martin Pipe, to a five-length victory in the Champion Hurdle at odds of 7/1. Two days later, he also rode the nine-year-old Mr. Mulligan, trained by Noel Chance, to a nine-length victory in the Cheltenham Gold Cup at odds of 20/1. All told, McCoy rode three winners at the 1997 Cheltenham Festival – the other being Or Royal, also trained by Martin Pipe, in the Arkle Challenge Trophy – which were sufficient to win him the leading jockey award for the first time.