In the history of the Cheltenham Gold Cup, which was inaugurated, as a steeplechase, in 1924, several owners have won what is, nowadays, the most prestigious race in the British National Hunt calendar three or more times. The three-time winners are, in chronological order, Frank Vickerman, owner of Cottage Rake, victorious in 1948, 1949 and 1949, and Jim Lewis, owner of Best Mate, successful in 2003, 2004 and 2005. Anne Grosvenor, Duchess of Westminster, owner of Arkle – who completed a notable hat-trick in 1964, 1965 and 1966 – went one better, courtesy of Ten Up in 1975 and is, in fact, the only four-time winner in the history of the Cheltenham Gold Cup.
However, beyond a shadow of a doubt, the most successful owner in the history of the Cheltenham Gold Cup was the Honourable Dorothy Paget, who was as eccentric as she was rich, but nevertheless amassed seven wins in the mid-twentieth century. The indomitable Miss Paget was, of course, the owner of Golden Miller, the most famous steeplechaser on the inter-war years, who completed an unprecedented five-timer in the Cheltenham Gold Cup in 1932, 1933, 1934, 1935 and 1936. She also owned Roman Hackle and Mont Tremblant, winners in 1940 and 1952, respectively.