His teammates included Rory Sabbatini and Camilo Villegas' caddie Gary Mathwes.

He was named to the Pac-10 Conference Team twice and inducted into the University of Arizona Golf Hall of Fame in 2000.

He turned professional later that year during the week of the Bell Canadian Open.

Gillespie started playing events on the Canadian Tour in 2002 but did not find immediate success.

He missed getting to the final stage of PGA Tour qualifying school in 2006 and considered quitting his golf career.