#5 Carlo Ancelotti
Tenure: 1 July 2009 - 22 May 2011 (691 days)
Matches: 109
Matches won: 67
Matches lost: 22
Win %: 61%
Honours: 2009 FA Community Shield, 2010 Premier League, 2010 FA Cup
Following his first trophy, the Community Shield in 2009, Ancelotti finished the season on a high by leading Chelsea to their third Premier League title and also winning the 2009-10 FA Cup. His team shattered records by becoming the first ever side in the Premier League to score more than 100 goals in a season.
The next season saw Chelsea nearly drop down below Champions League positions only to somehow manage to finish second behind runaway leaders Manchester United. However, second-finishes was not what Abramovich signed Ancelotti for, as two hours after their final Premier League match of the season 2010-11, Ancelotti was abruptly shown the door.