Tommy was one of five American golfers to qualify for the European Seniors Tour at the 1998 Qualifying School and has been a regular ever since. His best finish is still a share of sixth behind Brian Huggett at the 2000 Beko Classic but he had a chance to do better than that in the 2000 De Vere Hotels Senior Classic where he was tied seventh going into the final round before closing with a 76 that dropped him into a share of 24th place. His best performance of the 2001 campaign came when he finished tied for 12th at the AIB Irish Seniors Open. Tommy did not miss a single cut in 2000 but did miss out on the money in five events the following season.