#2 Avram Grant
Tenure: 20 September 2007 - 24 May 2008 (248 days)
Matches: 54
Matches won: 36
Matches lost: 5
Win %: 67%
Honours: -
After the discourteous exit of fan-favourite Jose Mourinho, Israeli Avram Grant faced a bitter and hostile welcome to the managerial seat at Stamford Bridge.
In his 248 days at the helm of the Chelsea ship, Avram Grant notably took the team to two cup finals, the League Cup final and the UEFA Champions League final in 2008. However, Chelsea ended up losing in both of them.
The first one, they lost 2-1 to Tottenham Hotspur at Wembley and the second was the famous defeat at the hands of their arch-rivals Manchester United in Moscow, where John Terry woefully slipped while taking the final penalty to hand Manchester United their third European Cup title.