He began his career with Fletcher Moss Rangers,[3] then moving onto Manchester United, and also represented England at under-17, under-19 and under-20 level.

After a year at Hull, he fell out of favour and went on successive loan spells to Burnley, Blackburn Rovers, Charlton Athletic and Leeds United throughout the 2012–13 and 2013–14 campaigns.

However he made just two FA Cup appearances for the club, and had loan spells with Barnsley and Doncaster Rovers in the 2015–16 season, before he was released by Ipswich in August 2016.

[4] He joined the squad for the UEFA Champions League match away to VfL Wolfsburg, and was named as an unused substitute.

[6] He made his League One debut in a 2–1 victory over Leyton Orient at Huish Park on 7 August, the first day of the 2010–11 season, after coming on as a 77th-minute substitute for Dean Bowditch.

[13][14] After spending over nine months on the sidelines, Stewart returned to first-team action on 19 November 2011, and scored his first goal in senior football in a 2–0 win at Derby County after cutting inside from the left.

[18] After heavy speculation, Stewart remained at Hull and played frequently for the rest of the 2011–12 season under manager Nick Barmby, and said he was "really happy" at the club.

[19] After a few appearances for Hull under manager Steve Bruce, new signings meant that Stewart's opportunities at the club became limited, and he joined Championship rivals Burnley on loan on 31 August 2012.

[23] He made his debut for Michael Appleton's "Riversiders" as a second-half substitute for Danny Murphy in a 3–2 defeat to Peterborough United at Ewood Park on 2 March.

[29] Speaking at the end of December, Charlton manager Chris Powell said he was optimistic of extending Stewart's stay at the club.

[34] He made 11 appearances during his loan spell at Elland Road, before new owner Massimo Cellino decided to cancel the permanent transfer.

On 31 August 2016, Stewart was released by Ipswich manager Mick McCarthy, having made just two FA Cup appearances throughout his two years at Portman Road.