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#3 Roberto Di Matteo (Chelsea)
Ever since his takeover of Chelsea in the summer of 2003, Roman Abramovich’s big dream was for the Blues to win the Champions League – and by 2012, he’d dispensed of no less than 6 managers in his attempts to complete this quest.
So it came as a massive shock when, in the 2011/12 Champions League final, it was a caretaker boss who delivered the famous trophy to Stamford Bridge.
Former Chelsea midfielder Roberto Di Matteo was appointed as the caretaker at Chelsea in early March 2012, following the sacking of Portuguese manager Andre Villas-Boas, who oversaw a diabolical reign that ended when most of the squad had been alienated by him. When Di Matteo took over, the Blues were in 5th position in the league and appeared to be way off the pace in the race for the Premier League title.
To claim Di Matteo oversaw Premier League success wouldn’t exactly be true – the Italian had mixed results in the league, winning 5 of his 11 matches, and the Blues ended the campaign in 6th – one place lower than when Di Matteo first took over. But elsewhere, the changes were dramatic.
Di Matteo’s first game in charge saw Chelsea defeat Birmingham City in an FA Cup 5th round replay, and the Blues then went on to win the trophy by defeating Liverpool 2-1 in the final. And of course, in European action Di Matteo’s Blues were fantastic.
They overcame a 3-1 deficit from the first leg of the second round against Napoli – a result that came under Villas-Boas – to win the second leg 4-1 to make it to the quarter-finals, where they then defeated Benfica 3-1 on aggregate.
In the semis, they defeated Barcelona in dramatic fashion – coming from 2 behind to draw 2-2 in the Nou Camp to make the final after winning the first leg at Stamford Bridge 1-0.
The rest is history, as Di Matteo’s Blues somehow defeated Bayern Munich in a penalty shoot-out – in Bayern’s home stadium to boot – to win the Champions League for the first time. Naturally, the unbelievable victory was enough to earn him a permanent contract – but that only lasted until the following November, when he was fired after some poor results.
