The 1995–96 season marked a transitional period for Chelsea. The arrival of Mark Hughes and Ruud Gullit brought excitement to Stamford Bridge, but the team finished 11th in the Premier League, maintaining a mid-table status for the third time in four years. Chelsea had a strong FA Cup run, reaching the semi-finals but losing 2–1 to Manchester United. Glenn Hoddle departed as manager at the season’s end to manage England, and Ruud Gullit was appointed player-manager, setting the stage for a new era by signing Roberto Di Matteo for a club-record £4.9 million.
The 1996–97 season was transformative for Chelsea under new player-manager Ruud Gullit. Using his international connections, Gullit signed stars like Gianfranco Zola, Gianluca Vialli, Roberto Di Matteo, and Frank Leboeuf. The team finished 6th in the Premier League and ended a 26-year trophy drought by winning the FA Cup with a 2–0 victory over Middlesbrough. Zola excelled, winning FWA Footballer of the Year, while Di Matteo scored in the final. The season was marred by the tragic loss of director Matthew Harding in a helicopter crash.
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