However, it was the 1999 Cheltenham Festival that saw Nicholls' breakthrough into jump racing's elite, winning three of the most prestigious steeplechases in National Hunt racing. Nicholls enjoyed a memorable meeting, collecting the Queen Mother Champion Chase with Call Equiname, the Arkle Challenge Trophy with Flagship Uberalles, and the Gold Cup with See More Business. However, it was not until the end of the 2005–06 season, after seven years of filling the runners up spot that Nicholls was finally crowned Champion Trainer for the first time, his eventual coronation coming after a long struggle for supremacy with multiple champion Martin Pipe.