The 1999 Cheltenham Gold Cup was a horse race which took place at Cheltenham on Thursday March 18, 1999. It was the 72nd running of the Cheltenham Gold Cup, and it was won by See More Business. The winner was ridden by Mick Fitzgerald and trained by Paul Nicholls. The pre-race favourite Florida Pearl finished third. The jockey-trainer partnership of Fitzgerald and Nicholls completed a big-race double, as they had also won the previous day's Queen Mother Champion Chase with Call Equiname.