Career
College and amateur
During his college years he also played with Cleveland Internationals in the USL Premier Development League. Professional
After spending the 2008 season playing with the Columbus Crew reserves, Gillespie joined the Cleveland City Stars of the USL First Division on April 20, 2009. He later signed with the Ohio Vortex on November 12, 2009 of the PASL where he played four seasons and was captain for two years.
During the 2010/11 season, Gillespie finished 5th in the league in assists with 17 overall after playing in 13 games.
In the following season, Gillespie scored 14 goals and added 14 assists.