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#1 Roberto Di Matteo
Roberto Di Matteo came to Chelsea with Andre Villas-Boas as an assistant coach in 2011. The club began the season well, but pressure began to mount on Villas-Boas after a string of poor performances led to Chelsea dropping out of the top four. The Portuguese manager was sacked in February 2012, and Di Matteo was promoted to the role of interim manager.
Di Matteo began his stint as manager with three successive victories, most notable of which was Chelsea's 4-1 victory over Napoli in the Champions League, which helped them overturn a 3-1 first-leg deficit. While Chelsea eventually finished 6th in the league under Di Matteo, the Italian manager won the Champions League and the FA Cup in that season.
Di Matteo was appointed as full-time manager in the following season but was promptly sacked after Chelsea became the first club to crash out in the group stage a season after winning the Champions League. He went on to manage FC Schalke in the Bundesliga, and is currently out of a job, after being fired from his position as Aston Villa manager in 2016.
