Ranking every Chelsea manager of the Roman Abramovich era from worst to best 

#4 Roberto Di Matteo (2012)

Juventus v Chelsea FC - UEFA Champions League

The only manager to take Chelsea to the pinnacle of European football, Roberto Di Matteo enhanced his own Chelsea legend by winning the Champions League with the Blues against all odds.

Even though he had a real lack of experience when he took over, Di Matteo, who was working as Villas-Boas' assistant at the time, certainly left his mark on the club.

A two-goal comeback against Napoli, and victories over Benfica, Barcelona, and eventually Bayern Munich in the Allianz Arena saw one of the greatest Champions League victories in the history of the competition.

However, in the league, the Blues finished sixth and only qualified for the following season's Champions League by winning the competition. The following season saw a poor start to life as the manager for Di Matteo, being knocked out of the Champions League at the group stage, which brought his time in charge to an abrupt end.

The Chelsea legend managed a win percentage of 57.1%, which plants him in the middle of the Abramovich era. However, being the only man to bring in the Champions League adds a lot of weight to his claim at being the best boss under Abramovich.