Born in Aberdeen and a product of the Highland Football League, Hamilton began his senior career as a part-time player with Banffshire club Keith, before moving to Premier Division side Dundee in January 1994.
He joined Heart of Midlothian in late 1996 and enjoyed a successful spell with them, scoring 33 goals in his two and a half years with the Edinburgh club and winning the Scottish Cup in 1998.
[4] In March 2003, Hamilton was told he could leave Tannadice,[5] and due to transfer window restrictions, he surrendered his professional status to sign as an amateur for Dunfermline Athletic for the remainder of the season.
On 29 August 2006, Hamilton re-signed for Dunfermline for an undisclosed fee,[11] playing 34 games and scoring five goals before signing for SPL side St Mirren on 30 January 2008.
Into his third decade as a professional footballer, Hamilton joined Arbroath in July 2010 on a one-year deal[16] but moved to East Fife the following January.