Carlo Ancelotti
Possibly the only man Abramovich employed who could arguably rival Mourinho as a great Chelsea manager, Ancelotti delivered the first ever domestic double to the club in his first year at the Bridge.
The current Paris Saint-Germain boss led the Blues to their first Premier League title since 2006 and also beat Avram Grant’s Portsmouth side in the FA Cup final.
Ancelotti had enjoyed plenty of success before joining the west London outfit after winning two Champions League trophies whilst at AC Milan.
However, failure to defend either the Premier League or the FA Cup in the Italian’s second season and a quarter-final exit in the Champions League saw Ancelotti dismissed in 2011.
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