He has done so by making what is still largely an ageing squad play much better than it did under the previous manager. It has happened before: Gus Hiddink somehow turned Drogba, Anelka and Malouda into a selfless front three who would make runs for one another.
At present Chelsea are poised between their past and their future. Saturday's cup win saw Mata making the first goal for Ramieres (new Chelsea) and Lampard making the second for Drogba (old Chelsea). The job for next season's manager is to complete that transiton.
And however good Di Matteo is at keeping old Chelsea on the road, it does not follow that he is the right man to build the new Chelsea.
Some will talk of loyalty, but sport is a pretty ruthless business. Both Robert Croft and Monty Panesar were dropped after heroic defensive innings that saved a test because their bowling was not good enough - and no one thought this was wrong. You have to think of what a team needs in the future.
Jonathan Wilson made the same point in the Guardian a couple of weeks ago:
Villas-Boas was appointed for a reason which was to manage the transition to a younger squad with a more dynamic style of play. That still has to happen: superbly as Chelsea played against Barcelona – and at times in the second leg against Napoli – the odd stint of dogged resistance from ageing limbs is not going to bring a league title.
Whether Villas-Boas tried to change things too quickly, whether his approach would ever have worked, whether he was over-confrontational or whether that was inevitable in the face of his squad's conservatism, is debatable, but what is not open to dispute is that change was necessary.
It still is – and whatever happens in Munich next month doesn't change that.Wilson's article drew parallels between Chelsea current situation and the decline and fall of Don Revie's Leeds.
That is worrying for any Chelsea fan - beating Revie's Leeds in the 1970 FA Cup final replay remains one of the key nights in the club's history - but at least no Chelsea manager had ever been accused of match fixing as Revie was.
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