Career
He began his career at Kilmarnock, before dropping into the Scottish Football League First Division with Airdrie United and then Ross County. He also had loan spells from Kilmarnock with Stirling Albion and Partick Thistle. As a striker who can also play on the wing, Di Giacomo made his Kilmarnock début in a 1–0 defeat of Street Mirren in July 2000.
He was loaned to Stirling Albion for part of the 2004-2005 season.
He again went out on loan in August 2007, this time to Partick Thistle. At Partick he scored twice.
Once against Berwick Rangers in a Challenge Cup tie and once against future club Greenock Morton in the league. He was released by the Rugby Park side in June 2008 and a week later was snapped up by Scottish First Division side Airdrie United.
He moved to Ross County on 1 June 2009.
Di Giacomo scored on his début for Ross County against his old club Airdrie United in the opening game of the 09/10 season. He continued his good start to the opening season with a goal against Inverness C.T. He joined Greenock Morton in June 2011, and scored four goals on his début against Stranraer in the Challenge Cup. On 1 May 2012, Di Giacomo confirmed that he would leave the club at the end of the season to go part-time.
In July 2012, he signed for former club Airdrie United.
His contract with Airdrie United was terminated by mutual consent in April 2013.