Ask him about Chelsea's historic Champions League triumph last season and his stock response is: "That's in the past."
But the Italian's almost relentless focus on the here and now wavered a little when it came to discussing his own memories of playing for the Blues against Manchester United.
Then, almost as quickly, the tunnel vision returned as he contemplated his first encounter with Sir Alex Ferguson's men since he became Chelsea manager.
Games against United have a special resonance for Di Matteo, not just because of what he called the "classic" nature of the fixture.
The former midfielder was part of the side that would travel to Old Trafford in the 1990s and almost invariably come away with a result.
That was when it was considered a fortress, and yet it was a ground where Di Matteo never tasted defeat.
It was also the scene of his final league game as a player, a 3-3 draw in September 2000 five days before he suffered the cruel leg-break that would ultimately end his career.
"I remember the games against Man United were always very competitive and quite balanced, to be honest, apart from one or two maybe," Di Matteo said ahead of Sunday's mouthwatering Barclays Premier League clash at Stamford Bridge.
"But they were always enjoyable games and games I was looking forward to playing because it was always playing against the best players - probably - in the league at the time and you're always looking forward to those games."
And were those the fixtures he missed the most when he was finally forced to admit defeat in his bid to play again?
"There are many things you miss when you're not a player any more," he said with an uncharacteristically wistful smile.
"Those daily training sessions with your team-mates and preparing, living towards the weekend for the game.
"But I'm over it. That's part of the past and I'm enjoying a different kind of challenge now."
A more daunting challenge, as he bids to mastermind a victory that would see Chelsea open up a seven-point lead over their perennial title rivals.
"It's a different role you play, that you have, as a manager," he said.
"Probably, the responsibility's much greater as a manager than a player.
"(There are) different kind of cycles in your life as well.
"You are older now and, you would think, a little bit wiser and more experienced."
Di Matteo will need all of that and more to outwit the man he considers still to be the best in the business.
Doing so may finally see the Italian get the credit he deserves, with last season's triumphs over the likes of Pep Guardiola and Jupp Heynckes still seen by many as a matter of luck more than judgment.
But he said: "I'm quite comfortable in my seat where I am and happy.
"I'm happy that the team is expressing itself well and that's my only focus, really.
"I said last season many times, my position is not that important.
"I know what job I have to do to try to prepare these guys for the next game as well as I can and I'm pretty happy about that."
So no ego then?
"I think that everyone has one but I'm comfortable in my position."
Di Matteo will sit a little less comfortably if his side suffers a second successive defeat after Tuesday's first major setback of the season at Shakhtar Donetsk.
And with John Terry suspended and Frank Lampard injured for the next three matches, it is vital Chelsea's new guard show the same resilience as their old warhorses in the coming days.
Sunday's match will be the second United fixture in a row both have missed following last season's 3-3 draw.
Prior to that, at least one of them had started every match against Ferguson's men since - spookily - Di Matteo's Premier League swansong.
"They are two influential players for us and we're going to miss them on Sunday," Di Matteo said.
"I think all the others will step up and we have to show that we are a team with character, a team with personality and we are showing the maturity to be able to play these big games."
Victory would cement Chelsea's status as title favourites but Di Matteo is as reluctant to focus on the future as he is on the past.
Asked if winning the Premier League would give him more satisfaction than winning the Champions League, he said: "Ask me at the end of the season."