Gillespie made his senior debut for Hamilton Academical on 15 August 2009, in a Scottish Premier League match against Kilmarnock.
[3] In May 2012, Gillespie urged manager Billy Reid to make him a first-team regular for the forthcoming 2012–13 season.
[4] In January 2012, after making an "impact" as a substitute in the previous game, Gillespie spoke publicly about his desire to start the team's next match.
[18] Gillespie was named club captain by manager Dougie Imrie, and made his first competitive appearance against Hibernian in the League Cup Group Stage.
[19][20] Gillespie would continue his positive start to life at Morton by scoring in the first league game of the season against his former club Hamilton.