After just a few games at United, Webb ruptured his achilles tendon while playing a match for England against Sweden in September 1989. Webb made his comeback for United as a substitute against Southampton on 24 March 1990, and made his first start since the injury the following Saturday, at home to Coventry City. Despite positive early indications - Reuters called him the "most influential player on the pitch" during a September 1990 clash with Luton Town - he never fully regained his pre-injury form, suffering from weight problems and other injuries. Webb was still a precise passer of the ball and was included in the England 1990 World Cup squad, having return to action during the second half of the 1989–90 season. He also helped Manchester United win the FA Cup in 1990, UEFA Cup Winners' Cup in 1991, and Football League Cup in 1992.