Tony earned his Tour card when he finished 11th in the 1999 Seniors Qualifying School in Turkey and went on to finish 36th on the 2000 Order of Merit, his best performance coming in the Ordina Legends in Golf in Holland where he finished tied third behind compatriot, John Grace. One of the steadiest performers on the circuit, the American missed just one cut in his rookie season, at the Senior British Open where he missed out by a single shot. Ended his 2000 season when he finished tied 11th at the US Senior Tour's Qualifying School, earning a conditional card for the 2001 US Senior Tour.