#2 Carlo Ancelotti – Chelsea, 2009
Carlo Ancelotti only managed in the Premier League for two seasons, but the Italian still showed bundles of class in his short time in England.
In his first season, Ancelotti led his Chelsea team to the Premier League title, a season in which they scored a record 103 goals along the way. He clinched the double too in his first season, beating Portsmouth to lift the FA Cup.
He was unable to capture any silverware in his second season in England, but his sacking still seemed very premature. Attaining Ancelotti’s services in the first place was quite miraculous considering what he achieved at Milan, winning two Champions League titles and finishing runner up to Liverpool in 2005.
He has now gone on to manage PSG, Real Madrid and Bayern Munich, winning another Champions League trophy with Real Madrid. Even though the Blues have been successful since, Roman Abramovich is still likely to be disappointed he let Ancelotti go so quickly.
Simply getting the Italian to manage in the Premier League made him one of the greatest coups in Premier League history.