Cheltenham Gold Cup was responsible for all of the first five horses to finish – Bregawn, Captain John, Wayward Lad, Silver Buck and Ashley House. The 1986 winner, Dawn Run, is the only horse to have ever won both this race and the leading hurdle event, the Champion Hurdle. One of the most popular horses to win the Gold Cup was Desert Orchid, a grey who won the event in 1989. The following year's running was won by Norton's Coin, whose starting price of 100/1 represents the race's longest ever winning price. The entire Cheltenham Festival was cancelled in 2001 because of an
The Thinker (horse) West Tip. In the 1988/9 season, The Thinker won a minor race at Kelso Racecourse and then took the listed Tommy Whittle Chase at Haydock Park, taking the lead at the second last and winning easily by twelve lengths from Kissane. He then finished third under top weight of 164 pounds in the Welsh National and fell at the tenth fence in the Cheltenham Gold Cup. On 8 April, The Thinker again carried 164 pounds when top weight for the 1989 Grand National. Ridden by Simon Sherwood, he lost his position on the second circuit but stayed on strongly in