8. Sacking Roberto Di Matteo
Roberto Di Matteo succeeded the unfortunate Andre Villas-Boas as Chelsea boss on a caretaker basis in March 2012, another surprising decision given the Italian had only managed Milton Keynes Dons and West Bromwich Albion prior. Yet he had worked admirably under Villas-Boas as an assistant prior and his stature at the club was already high given his playing career at Stamford Bridge. In the end in fact, he did a much better job than anyone dared possibly expect of him. He led the team to the FA Cup and also became the first ever Blues manager to win the Champions League - yet still he was astonishingly relieved of his duties after just 8 months - one fewer than Villas-Boas despite being decidedly more successful than his counterpart. It begs the question - what exactly do you have to do to stay in a job at Chelsea? There is very little else Abramovich could possibly have expected from him.