He never played for Hearts, and made his debut on loan back at Stenhousemuir in the Scottish Football League Second Division, where he later represented Arbroath and Brechin City.
[2] He was first included in a matchday squad on 15 May 2011, remaining an unused substitute as they concluded the Scottish Premier League season with a 2–1 defeat at Dundee United.
[17] On 29 November, Hamilton headed the opening goal away to Annan Athletic in the Scottish Cup fourth round, but it ended in a 1–1 draw;[18] ten days later he scored again in the replay, a 4–2 victory.
[20] Hamilton played 32 League One games in his only season at Brechin, and also took part with them in the play-offs for promotion to the Scottish Championship, where they lost 2–1 on aggregate to Alloa Athletic in the semi-finals.
[22] He made his debut on 25 July, playing the full 90 minutes as they won 1–0 at Highland League team Brora Rangers in the first round of the Challenge Cup.
[24] He scored his first Alloa goal on 19 September, a last-minute equaliser against Rangers at the Indodrill Stadium,[25] and added a second on 9 February 2016 to start a comeback to earn a 2–2 home draw against Greenock Morton.
[27] In his first match back for the Red Lichties, he scored a last-minute equaliser to earn a 1–1 draw at home to Championship club Dundee United in the group stages of the League Cup.