The 42-year-old's astute tactics, mixed with plenty of luck and some resolute defending, secured a 1-0 win over reigning European champions Barcelona at Stamford Bridge in the first leg of their semi-final on Wednesday.
Despite Barca enjoying 72 percent possession and 19 attempts on goal, Chelsea's victory, coupled with their 5-1 thrashing of London rivals Tottenham Hotspur in the FA Cup semi-final on Sunday, have put Di Matteo's men within sight of two trophies.
The likes of Frank Lampard, 33, Didier Drogba, 34, captain John Terry, 31, Ashley Cole, 31, and out-of-form striker Fernando Torres all looked spent, with the former especially seemingly peripheral to Villas-Boas's long-term plans.
After Wednesday's win, which came courtesy of a Drogba goal just before half-time, Di Matteo said: "In the past, a lot of people have had the opinion that our boys were over the line and too old to play at this level.
"It was not just Didier, but a lot of players in our squad, that they said couldn't play two games in such a short period of time. They gave their answer on the pitch."
Many experts predict that Barcelona will recover and reach the final in Munich next month, but even if they do, Chelsea's billionaire Russian owner Roman Abramovich would be taking a huge gamble in replacing Di Matteo at the end of the season.
While it has been widely reported that Abramovich wants Barcelona's manager Pep Guardiola to coach his side or some other "big name", the Russian may have the answer to his dreams of winning the Champions League already in place.
