10. Roberto Di Matteo
Cost: £4,900,000 Appearances: 175 Goals: 26 As a player, Di Matteo won 6 honours at Chelsea, and also scored the fastest ever goal in an FA Cup final. This would all be dwarfed, however, by his recent stint as manager, as he surprised the world in taking Chelsea to unlikely Champions League glory. Despite his somewhat surprising sacking by the Blues just a few months after delivering to Roman Abramovich the trophy that he has elaborately obsessed over for almost a decade like some sort of mid-meltdown tv detective, Di Matteo's two spells at the club more than safely label him as a Chelsea legend. Sources:
BBC