The Italian took his place at a Champions League press conference yesterday as the Blues manager ahead of this evening's crunch second leg against Napoli, little more than a year after getting the sack from West Brom.
By any stretch, it is a remarkable turnaround in his fortunes. The Italian coach may well be thinking that this is his big chance to prove he is the man to take the job on full-time.
If none of Roman Abramovich's preferred candidates are available in the summer then the former Chelsea midfielder who looks like a Gerry Anderson marionette could be pulling the strings for the Russian's team on a permanent basis.
Manage to overturn the two-goal aggregate deficit against the Partenopei — making it three wins out of three since taking charge - and he will be a club hero. Should Chelsea fail, then few can point the finger at him for failing with a team left demoralised and disorganised by Villas-Boas.
When Guus Hiddink had his stint as interim manager back in 2009, the clamour for him to take the job on a permanent basis was apparent long before he lifted the FA Cup. Hiddink enjoyed such an unimpeachable reputation while in England that not even prancing around Stamford Bridge with the cast of Sister Act: The Musical could damage his image. Just take a look at the pics, and ask yourself how many other managers could get away with doing the same.
Di Matteo has not come into the job with anything like the track record of Hiddink. While the European Cup-winning Dutchman was winning the FA Cup at Chelsea, Di Matteo was impressing in his first year in management at League One MK Dons. The following year he took over at West Brom, and 12 months after that he was in the dugout for the Baggies' first fixture back in the Premier League at Stamford Bridge, where his team were thrashed 6-0. He was sacked last February after a dismal run of results, with Roy Hodgson doing so well at The Hawthorns since replacing him vindicating the decision.
Despite that, he will be hoping to make the most of the latest step in the alarmingly steep (albeit split) upward trajectory of his management career. Reaching the latter stages of the Champions League and finishing in the top four would be as good an audition as he could hope to give for the job full-time.
Not, it seems, that anyone cares. For sat next to Di Matteo at the aforementioned press conference was John Terry, back from injury and ready to sort out the mess which had been made in his six-week absence.
Of the 15 or so questions asked in English during the presser, only one of them was directed at Di Matteo. It was all about JT.
Facing the media for the first time since he was stripped of the England captaincy and with his old team-mate "Robbie" next to him, anyone uninitiated in the ways of Chelsea would have assumed that the defender was the man in charge and not the slightly bemused-looking Italian sat next to him.
Terry, who helped Chelsea keep a clean sheet upon his return to the team for Saturday's 1-0 win over Stoke, took the opportunity to ridicule the notion that Chelsea's senior players played any part in Villas-Boas's sacking.
Refuting the idea that here is too much player power at Chelsea whilst he overshadowed his manager, Terry said: "We win and lose together at this club - we're all responsible for the results we have. As for the senior players running this football club, that's nonsense. That's just the perception from outside. Roman and the board make the decisions.
"On the football pitch, that can affect what happens upstairs of course. If we don't win matches, the board step in.
"People speculating from various different clubs or previous managers, that's complete nonsense."
While Terry was not fooling anyone with a line which could have been a direct quote from his reaction to the sacking of either Luiz Felipe Scolari or Carlo Ancelotti, he was certainly speaking the truth when he said that progressing from this tie would go down as "one of the great nights in Chelsea history".
The issue is not so much how Chelsea will score the two goals needed to overturn their 3-1 first-leg deficit and go through, but how on earth they will stop Napoli from scoring.
The attacking triumvirate of Edinson Cavani, Ezequiel Lavezzi and Marek Hamsik are a fearsome unit who have made Napoli the most clinical team in this season's Champions League, with a shots-to-goals ratio better than one in five.
They put six past Cagliari on Friday night, and that was with Cavani and Christian Maggio — the wing-back who gave Ashley Cole such a torrid time in the first leg — on the bench for the first hour.
If Chelsea manage to overcome such a test and reach the quarter-final draw, you can be sure Terry will be lapping up the plaudits. Should they fail, Di Matteo will likely see the window of opportunity slammed shut on him.
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QUOTE OF THE DAY: "I was primarily duped. My advisers were duped, the bank was duped, the shareholders were duped. We've all been duped. I always remember someone said, 'Does it pass the sniff test?' He was Scottish, he wasn't a foreigner, he was supposedly a Rangers supporter, he had the money. There is a Stock Exchange offer document there. If you can't believe that, what can you do?" — David Murray doesn't mince his words in expressing his regret at selling his majority shareholding in Rangers to Craig Whyte last year.
FOREIGN VIEW: "I'm very happy for him because I have seen games where he has been substituted and the crowd have jeered him. The fact that he scores goals is a reflection that the team is playing well. A striker needs security and confidence and he gets that from the team." — Bayern Munich coach Jupp Heynckes praises Mario Gomez, who scored his second hat-trick in a week as the Bavarian giants drubbed Basel 7-0 in the second leg of their Champions League tie.
Jim White, Andy Mitten and Des Kane will all be filing their latest blogs throughout the day, Zonal Marking's Tactical Brain will be dissecting one of the weekend's Premier League fixtures and Steve Bruce is the latest manager to take our quickfire 60 Seconds quiz.