Roberto Di Matteo – Chelsea, 2012
The departure of Andre Villas-Boas left the relatively unheard of (managerially) Di Matteo, while still technically under the role of caretaker, with the duty of bringing success to a club which found itself outside the top four and were down 3-1 on aggregate to Napoli in the Champions League elimination stages.
In his opening three games, Di Matteo clocked up a fifth round FA Cup win over Birmingham City, a Premier League win against Stoke and most impressively, overturning the 3-1 aggregate scoreline in the Champions League to defeat Napoli 4-3 over the two legs.
The Italian and his Chelsea side went on to defeat Tottenham 5-1 in the FA Cup semi-final, and subsequently achieve his first piece of silverware as the West Londoners defeated Liverpool in the FA Cup final just 32 days after his appointment.
With a goal already under his belt, the super sub was after his brace.
Defeating Benfica, Barcelona and ultimately Bayern Munich on penalties on the road to the club’s first ever Champions League glory, still technically as a caretaker coach, saw Di Matteo achieve FA Cup and Champions League glory after just two and a half months in charge.
However, in keeping with the supernatural Italian managerial curse, despite being third in the Premier League, Chelsea’s 3-0 loss to Juventus in the Champions League brought with it their elimination, and Di Matteo’s controversial sacking after an eight-month spell that reaped two major titles.
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