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
Denman (horse) kept him handy and out of trouble, but in the home straight, Diamond Harry matched strides and eventually passed Denman to win, with Burton Port staying on well into second place. Denman's trainer, Paul Nicholls, after the race was delighted with the run and informed the racing public that Denman would not be seen until the Cheltenham Gold Cup in March, where he would try to regain this prize which he last won in 2008. On 20 February 2011, Nicholls reported that Denman had had a wind operation shortly after the Hennessy. The trainer felt that the horse had not