Who was the last amateur jockey to win the Cheltenham Gold Cup?

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.