An ankle injury kept Sinclair out of the side at the beginning of the 1992–93 season. He returned to the first team in September in a televised match against Manchester City that Chelsea won 1–0. However, Sinclair's mentor, Paul Elliott, suffered a career ending injury in the match. Despite this setback Sinclair managed to make a total of thirty-nine appearances in all competitions, primarily at left-back, as Chelsea finished in mid-table. His impressive performances earned him the Chelsea Player of the Year award in 1993. Glenn Hoddle was appointed as manager for the 1993–94 season, replacing David Webb, and preferred using a sweeper system which saw Sinclair convert into a central defender. He excelled in this position, however, the team's performances were poor and the side were involved in a relegation battle for the most of the campaign. Despite their poor league form Chelsea made it to the 1994 FA Cup Final against Manchester United at Wembley Stadium, their first major cup final since 1972. Chelsea could not prevent United from claiming the league and cup double in a 4–0 defeat, with Sinclair conceding the penalty for a foul on Andrei Kanchelskis in the second-half, which was scored by Eric Cantona to make it 2–0. Despite the defeat Chelsea qualified for the next seasons UEFA Cup Winners' Cup as runners-up, their first European campaign in over twenty years.