Fitzgerald was
leading jockey at the Cheltenham Festival twice. On the first
occasion, in 1999, he achieved a notable double on Call Equiname and
See More Business, both trained by Paul Nicholls, in the Queen
Mother Champion Chase and the Cheltenham Gold Cup, respectively. That
year, he also won the Triumph Hurdle on Katarino and the now-defunct
Cathcart Challenge Cup on Stormyfairweather, both for Nicky
Henderson. On the second, in 2000, he won the Arkle Challenge Trophy
on Tiutchev, the Festival Trophy on Marlborough, the Stayers' Hurdle
on Bacchanal and the Cathcart Challenge Cup on Stormyfairweather
again; all four winners were trained by Nicky Henderson.
Remarkably, despite a 15-year association with Nicky Henderson – who is, nowadays, the leading trainer in the history of the Champion Hurdle, with eight wins – Fiztgerald never won the two-mile hurdling championship. In fact, in twelve attempts, two third places, on Blue Royal in 2000 and Afsoun in 2007, were the best he could muster.