Monday sees Blues boss Di Matteo take a team to his homeland for the first time in his coaching career and there can surely be no better way to go back than as a European champion.
The past eight months have seen the 42-year-old catapulted from virtual managerial obscurity in Italy into the exclusive pantheon of those to have won club football's ultimate prize.
Only six of his compatriots have performed the same feat as Di Matteo down the years and none of them managed it with a foreign club.
He may not enjoy being the centre of attention but it is fair to say all eyes will be on Chelsea's manager ahead of their crunch Group E game at Juventus.
Asked if he was returning home full of pride, Di Matteo said: "I'm proud to have led this club to that trophy.
"Wherever we go, it's a moment where we are a good club.
"We've shown it and we have to show it again."
Tuesday's match at Juventus Stadium is precisely the sort of game in which Chelsea have risen to the occasion down the years, thanks largely to their so-called 'old guard'.
But with Didier Drogba having ridden off into the sunrise, John Terry injured and Frank Lampard unlikely to be risked, the onus is firmly on the new wave to come to the rescue.
They initially suggested they were incapable of doing so, going within seconds of leaving Chelsea arguably needing to beat a side whose 49-game unbeaten run in Serie A only ended earlier this month.
But Victor Moses's last-gasp winner against Shakhtar Donetsk a week and a half ago ensured the Blues' destiny remained firmly in their own hands with two Group E games to play.
A draw against Juve and what is expected to be a routine win over Nordsjaelland would ensure they maintain their record of having never failed to reach the knockout phase when they have qualified for the Champions League.
But should they lose on Tuesday, they would find themselves on the brink of becoming the first holders to crash out before Christmas.
Italian champions Juve are in just as precarious a position and it looks likely this week's result will seal one of the two clubs' fate in what has been arguably the most open Champions League in history.
Only Manchester United boast a 100% record after four group games, with the likes of Barcelona, Real Madrid, Bayern Munich and AC Milan joining Chelsea in suffering defeats.
Di Matteo claimed the Champions League was becoming more of a lottery than ever.
"Every year now, it's becoming more and more difficult," he said.
"We had APOEL, who showed how a relatively small club can do very well in the Champions League.
"Every season, you see clubs surprising in the Champions League.
"It becomes more competitive and difficult every season, and clubs with new investment and traditional clubs like Juventus coming back after many years, often ending up in pots two, three or four.
"It makes it very difficult."
Having splurged £80million building on last season's triumph, it is unlikely Chelsea owner Roman Abramovich would be as philosophical about the prospect of his club falling at the first hurdle.
With Pep Guardiola still waiting in the wings, there is no telling how the Russian would respond, even when it comes to a conquering hero.