Manchester United Born in
Manchester, Stewart began his football career with
Manchester United and signed as a trainee in 2007. After working his way up through the
youth and reserve teams, he was promoted to the first-team by manager
Alex Ferguson in December 2009. He joined the squad for the
UEFA Champions League match away to
VfL Wolfsburg, and was named as an unused substitute. In July 2010, Stewart joined
Yeovil Town on a six-month
loan. 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. Stewart returned to
Old Trafford in October after making only five appearances for
Terry Skiverton's "Glovers".
Hull City On 25 November 2010, Stewart joined
Hull City of the
Championship on loan until 4 January 2011. He made his debut for the "Tigers" on 27 November in a 2–2 draw away at
Middlesbrough. Hull City extended his loan until the end of the
2010–11 season after a string of good displays. On 31 January 2011, Stewart signed for Hull City on a permanent basis, for a fee believed to be in the region of around £300,000. However, on 19 February, he suffered cruciate ligament damage in a 1–1 draw at
Ipswich Town, which ruled him out for the remainder of the season and the start of the following season. 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. He scored his second goal for Hull in a 3–1
FA Cup win over Ipswich Town at the
KC Stadium on 7 January. Following some good performances after his comeback from injury, Stewart was subject to a bid from
Leicester City – managed by former Hull boss
Nigel Pearson, understood to be £1.5 million, which was rejected, with Hull warning that the winger was "not for sale". 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. 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. After starting two out of three of his first games at
Turf Moor, his appearances became increasingly limited and he failed to play again for the "Clarets" after
Sean Dyche replaced
Eddie Howe as manager; as a result Hull manager Bruce commented that "he's probably going to come back to us in January and we'll see where things go. It's been disappointing for all parties. He went out to play games with Burnley and that's just not happened for him". Upon returning to Hull in January, Stewart started in a 1–1 home draw with Leyton Orient in the FA Cup, following which Bruce was critical of Stewart's match fitness. On 1 March 2013, Stewart joined Championship rivals
Blackburn Rovers on loan for the remainder of the 2012–13 season. 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. After Hull City's promotion to the Premier League at the end of the
2012–13 season, Stewart was strongly linked with a move to
Scottish Premier League club
Celtic. On 2 September 2013, Stewart moved on loan to Championship club
Charlton Athletic until January 2014. He scored on his debut for the "Addicks" on 17 September, in a 2–1 defeat at
Huddersfield Town, after coming on as a 68th-minute substitute for
Richard Wood. He made his first start on 28 September against his former club Burnley, playing the first 83 minutes of a 3–0 away defeat. On 9 November, Stewart scored a volley from distance in a 4–2 defeat to
Leeds United at
The Valley. Speaking at the end of December, Charlton manager
Chris Powell said he was optimistic of extending Stewart's stay at the club.
Leeds United loan On 9 January 2013, Stewart signed an initial three-month emergency loan at Championship side Leeds United, with a permanent deal on a three-year contract starting at the end of the
2013–14 season; he was the first signing made by manager
Brian McDermott under the brief ownership of the Sports Capital consortium. The deal was initially only on a loan basis to circumvent
FIFA rules that prevented Stewart from signing a permanent contract at a club after already representing two other clubs (Hull City and Charlton Athletic) in the
2013–14 season. He made his debut for the "Whites" on 11 January, in a 6–0 defeat at
Sheffield Wednesday. He made 11 appearances during his loan spell at
Elland Road, before new owner
Massimo Cellino decided to cancel the permanent transfer. Stewart sued Leeds United, and was awarded £750,000 in compensation, the entirety of his three-year contract.
Ipswich Town On 1 July 2014, Stewart joined Championship side Ipswich Town on a three-year contract. Just before the beginning of the
2014–15 season, he broke his jaw and was ruled out of action for the first six weeks of the campaign. Stewart made his debut for the "Blues" as a 62nd-minute substitute in a 1–1 draw at
Southampton in the FA Cup on 4 January 2015. On 21 March, Stewart joined League One side
Barnsley on loan until the end of the
2014–15 season. He made four appearances for
Lee Johnson's "Tykes", before returning to Ipswich. On 28 August 2015, Stewart joined
Paul Dickov's
Doncaster Rovers on loan until January. He made his debut the following day as a substitute in a 2–0 win over
Fleetwood Town at the
Keepmoat Stadium. On 14 January, Stewart extended his loan to the end of the
2015–16 season. He credited Rovers manager
Darren Ferguson for his decision to stay on at the club, and Ferguson said that Stewart offered good cover for wing-back
Felipe Mattioni. However two days later Stewart was hospitalized with
whiplash after he landed on his head during a match against
Gillingham. He made a total of 28 appearances for "Donny", scoring four goals, as the club were relegated out of League One. 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.
Lincoln City Stewart had trials at Charlton Athletic and
Port Vale during summer 2017. On 24 October 2017, Stewart signed for
Lincoln City. His contract with Lincoln was mutually terminated at the end of the 2017–18 season. Stewart retired from professional football at the age of 28. ==International career==