Playing Career
Stein started his career with Edgware Town before signing for Luton Town in 1977 under David Pleat. This was the first of two spells with the club, where he made 427 appearances and scored 130 goals.
Initially a winger, he soon moved into a central striking role where he formed successive prolific partnerships with Bob Hatton and then Steve White as Luton won the Second Division Championship in 1981/2. The following season his striking partner in the top flight was a youngster, Paul Walsh, and Luton took the league by storm with a flurry of bravura attacking performances in the early weeks of the season, including 5-0 and 5-3 home victories over Brighton and Notts County, and a 4-4 draw away to Stoke City. To cap it all Luton then went to Anfield and surprised the Liverpool fans with Stein scoring twice past Liverpool keeper Bruce Grobbelaar, the game eventually finishing 3-3. The initial excitement and promise of the season faded somewhat over the winter as Luton struggled, not least because of Stein missing a substantial part of the season after breaking his foot in December, and by the last game of the season Luton needed to win away at Manchester City to stay in the top division and condemn City themselves to relegation. Stein returned for the game despite lacking match fitness, and played his part with a cross four minutes from time which fell to Raddy Antic to score the winner. The game is primarily remembered for an excited Luton manager, David Pleat, gambolling across the pitch at the final whistle to hug his players.
Strike partner Walsh moved to Liverpool at the end of the 1983-4 season, and Stein then formed an equally strong partnership with Mick Harford. His finest hour came on 24 April 1988 when he scored two goals, including the late winner, in Luton's 3–2 League Cup Final victory against Arsenal.
Stein was released at the end of the 1987–88 season, joining French team Stade Malherbe de Caen. In 1990 he signed for another French team, Annecy. He rejoined Luton for the 1991–92 season, but Luton were relegated at the end of the season, ending a run of ten successive seasons of top flight football, all but three of which Stein was an integral part of.
He signed for Barnet in 1992, retiring as a player at the end of the 1992–93 season.
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