[2] In the 2006–07 season, Stewart made one appearance as a substitute in Falkirk's 5–0 Scottish League Cup victory over Cowdenbeath, scoring within two minutes of his professional debut.
[3] Ahead of the 2007–08 season, Stewart, along with Brian Allison, Scott Arfield and Chris Mitchell impressed manager John Hughes in a pre-season friendly.
Shortly making his league debut for Falkirk, Stewart continued to remain on the substitute bench towards the end of the season and made two more appearances.
[9] Stewart was expected to make his Europa League debut against Vaduz in July 2009, but a groin injury prevented him from doing so; eventually, Falkirk were eliminated after losing 2–0 in the second leg.
During the season, Stewart would score four braces, including in a 4–3 win over Hearts in the last 16 of Scottish League Cup on 21 September 2010.
With his Falkirk contract at an end, Stewart signed for English League Two club Bradford City on 1 July 2011, alongside Chris Mitchell.
[15] Shortly after the move, Falkirk announced their intention to claim a training and development compensation fee for Stewart, who was under the age of 24, from Bradford.
Three days later, in the first round of the League Cup in a West Yorkshire derby with Leeds United, Stewart provided an assist for Jack Compton in a 3–2 loss.
He returned to Scotland on 27 January 2012, signing a loan deal with Scottish First Division side Hamilton Academical.
[19] He made his debut on 14 February 2012 in a 2–1 loss to Morton[20] A month later, on 20 March 2012, Stewart scored his first goal since his return to Scotland in a 3–1 win over Dundee.
[41] Stewart scored his first league goal for the Sons in a 2–1 victory against Brechin City in September 2017, having come on as a half-time substitute.