Stewart signed his first professional contract with Falkirk in 2007, after coming through the Bairns’ youth academy. At 18 years-old he went out on loan to Berwick Rangers during the 2007-08 season, and made his senior debut against Ayr United in January 2008. He signed a one year extension with Falkirk ahead of the 2009-10 season, and made his first team debut for the Bairns in November 2009, coming on as a late substitute against Celtic. During the 2010 January transfer window he went out on loan to East Fife until the end of the season, and after becoming a regular in their line-up he returned to Bayview for a second loan spell at the start of the 2010-11 season.
He began to appear regularly after his return to his parent club in January 2011, and over the next three seasons he made 88 appearances for the Division One side, and was part of the side that won the Challenge Cup in 2012 and then reached the Semi-Finals of the Scottish Cup in 2013. Although offered a new deal with Falkirk, Stewart decided to move to English outfit Fleetwood Town in June 2013.
In his first season with Fleetwood, Stewart made 48 appearances as the club won promotion to League One after reaching the Play-Offs and winning the final against Burton Albion at Wembley Stadium. He lost his first team place the following season, and spent two months on loan at Northampton Town before returning for nine further games with Fleetwood.
After being released in May 2015, he returned to Scotland to sign a two year deal with Ross County, and was part of the side that went on to lift the League Cup in March 2016. After more than 30 appearances, he was released midway through his contract, and signed for United on a one year deal to try and help the club regain their Premiership status.