Background
Gillespie was born in Oshawa, Ontario.
Gillespie was born in Oshawa, Ontario.
He attended the University of Arizona and was the only freshman to play in every tournament.
He was a heralded junior golfer in Canada, playing in the 1995 and 1996 Canadian Junior National Teams and was named the top Canadian golfer for those two years. 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 Professional Golf Association Tour qualifying school in 2006 and considered quitting his golf career.
He has made only 1 of 4 cuts on the Canadian Tour in 2008. Gillespie will play on the Web.com Tour in 2014 after earning his tour card through qualifying school.
1995/96 Canadian Junior National Teams 2000 Pac-10 Conference Team at University of Arizona 2002 Myrtle Beach Barefoot Championship Amateur Eisenhower Trophy (representing Canada): 2000.