He has two Nike Tour victories and has finished runner-up in two PGA Tour events including the 1996 Players Championship. Tolles led by two strokes after three rounds but a final round 72 left him in a tie for second place, four behind Fred Couples.
Tolles had a pair of third-place finishes in major championships. He finished solo third at the 1997 Masters Tournament. Tolles also finished tied for third at the 1996 PGA Championship.
Tolles finished T-5 at the U.S. Open in 1997 and finished 1 spot out (11th) from making the 1997 U.S. Ryder Cup team.