Blackpool Stewart started his career as an apprentice with
Blackpool, turning professional in October 1981. He made his debut for the Seasiders in a home draw with
Rochdale on 10 February 1982. For the remainder of the season, he alternated between midfield and forward. It wasn't until
Sam Ellis became manager that Stewart found his true role, at centre-forward, helping Blackpool win promotion from the Fourth Division in 1985. In his final season (1986–87) with the Tangerines, he notched-up 21 goals and helped
Mark Taylor net 14 goals, although it wasn't enough to mount a Third Division promotion challenge.
Manchester City After over 200 first team appearances, he joined
Manchester City in March 1987 for a fee of £200,000, then a welcomed record for hard-up Blackpool, but he was unable to keep City in the First Division. On 7 November 1987 he was one of three players, the others being
David White and
Tony Adcock to score a
hat-trick in a 10–1 victory over
Huddersfield Town in the Second Division. Stewart scored a total of 24 goals for City that season, as they reached the quarter-finals of the
FA Cup, but were unable to win promotion back to the First Division, and a move from
Maine Road was looking inevitable.
Tottenham Hotspur Terry Venables signed Stewart for
Tottenham Hotspur in June 1988, paying £1.7million (a portion of which went to his first club, Blackpool). At the time it was one of the highest fees paid by an English club, and the highest for a Second Division player. Stewart made his debut for Spurs on 1 October 1988, as a substitute in a 2–2 draw at home to
Manchester United, missing a stoppage time penalty. Bought as a striker and scoring 12 goals in his first league season at
White Hart Lane, when his goals dried up, he was successfully converted to a midfield role. This came about during a match with Luton at White Hart Lane in December 1990, with Spurs losing Nayim and Pat van den Hauwe to red cards (and Luton being down to ten men), he dropped back and was the most influential player in the match, scoring both goals in a 2–1 win. He was part of a Tottenham midfield which also included
Nayim,
Paul Gascoigne and
Paul Allen, backing up the strikeforce of
Gary Lineker and
Paul Walsh. On 5 January 1991, Stewart returned to
Bloomfield Road when Tottenham beat Blackpool 1–0 in the Third Round of the
FA Cup. It was the only time Stewart faced his first club. He would go on to score Spurs' first goal in the
1991 FA Cup Final win against Nottingham Forest, and was generally regarded as the Man of the Match.
Liverpool After speculation over the summer of 1992 that he would sign for
Manchester United or return to
Manchester City, Stewart was transferred to Liverpool in July 1992 for £2.3million, but injuries and lack of form plagued his time at
Anfield. He became their second striker alongside
Ian Rush after
Dean Saunders was sold to
Aston Villa in September, but managed just one league goal (against Sheffield United on his Anfield debut) from 24 games as Liverpool spent most of the season struggling in the new
Premier League before finishing sixth. On a rare positive note at Anfield, he scored twice for the Reds in their
European Cup Winners' Cup first round first leg victory over
Apollon Limassol on 16 September 1992. A proposed return to Manchester City, who expressed an interest in re-signing him in July 1993, never took place. He played just eight league games in
1993–94 as new arrival
Nigel Clough and then rising star
Robbie Fowler took his place alongside Rush, and went out on loan to
Crystal Palace, helping them return to the Premier League at the first attempt as Division One champions. He never played for Liverpool after the 1993–94 season, although he remained contracted to the club (and assigned the number 8 squad number for another season until it went to
Stan Collymore) until March 1996. Stewart scored just three goals during his spell at Liverpool.
Later career He had loan spells at
Crystal Palace (January 1994),
Wolverhampton Wanderers (September 1994),
Burnley (February 1995) and
Sunderland (August–November 1995), before joining
Sunderland on a free transfer in March 1996 and helped them win promotion to the
Premier League as Division One champions. He was unable to keep them in the Premier League and after their relegation he signed for
Stoke City. Stewart's spell at Stoke City was not a successful one as he played 25 times in
1997–98 scoring three goals and ended with Stoke suffering relegation to the third tier. Stewart then signed for non-league side Workington, scoring 15 goals in 55 games over two years, and helping them win promotion from the
North West Counties League in his first season, before retiring from playing completely at the end of the
1999–00 season with Workington re-established in the
Northern Premier League First Division. Stewart remains one of the very few players to have the distinction of playing in a north London derby, a Manchester derby, a Merseyside derby and a Northeast derby. ==International career==