Career
Stewart began his footballing career at Rangers" Academy until he was 13, and played for Hearts, but was also released due to his height. He then trained with Falkirk and Stirling Albion for almost a year, before joining Syngenta Amateurs Football Club in 2007. In July 2010 Stewart signed with Cowdenbeath, in the Scottish Championship.
He made his division debut on 7 August, in a 0–2 home loss against Ross County.
On 6 November he scored his first professional goal. He finished his first professional season as the club"s top scorer, with 9 goals.
On 7 April 2014, it was confirmed Stewart signed a pre-contract agreement with Dundee, officially joining the club on 1 June. He scored on his debut as Dundee beat Peterhead 4–0 in the first round of the Scottish League Cup on 2 August 2014.
On 16 January 2015, he signed a new contract until 2017.
On 11 February 2015, Stewart was named as SPFL Player of the Month for January 2015, after scoring five goals in seven matches during the month.