Just 10 weeks after taking over at Stamford Bridge following the sacking of Andre Villas-Boas, Di Matteo has already overseen a string of notable performances including an unforgettable semi-final win over Barcelona.
But the Italian believes that orchestrating a win over Bayern on their home ground on Saturday would represent his greatest triumph as he attempts to pull together a Chelsea side decimated by injuries and suspensions.
Chelsea will be without suspended captain John Terry and fullback Branislav Ivanovic as well as inspirational midfielder Ramires and Raul Meireles.
Di Matteo is also sweating on the fitness of defenders Gary Cahill and David Luiz along with midfielder Florent Malouda.
Given the circumstances, Di Matteo agreed he faced the most challenging tactical assignment of his career.
"With all the problems that we have it's certainly causing me a headache," the 41-year-old said.
Despite overseeing a rebound in Chelsea's fortunes, which included an FA Cup victory as well as their passage to the Champions League final, Di Matteo has yet to be given any assurances about his long-term future at Chelsea.
Chelsea say no decision on a long-term successor to Villas-Boas will be taken until the season has ended, and Di Matteo insists he is happy to wait.
"I'm very relaxed about it," Di Matteo said.
"I just have a big drive and a big motivation to do something extraordinary for this club and that's all I want to do. And whatever comes afterwards -- well, there's always a reason for things that happen."
He also brushes off suggestions that failure to land the top job would be a bitter pill to swallow if Chelsea were successful on Saturday.
"I'd be absolutely delighted to win the Champions League trophy for this club and I'd be very happy for the players," he said.
"We've worked so hard to reach this goal and have tried many many times to win it. I don't think about myself.
"It's a big game for the club and our players. It's a massive game. But we have to go into it with the knowledge that we have the quality and experience to win it and that's all."
He also dismissed criticism of Chelsea's tactics in the semi-finals, when their 10 men managed to mount a stunning rearguard action against Barcelona in the Camp Nou before clinching a 3-2 aggregate win.
"I wasn't annoyed (by the criticism)," Di Matteo said. "I was very happy that we beat Barcelona. Football is about playing football and scoring goals, and we scored more goals than them. And we probably scored the best goal as well.
"I understand from the neutral point of view that people may prefer other styles, but we've just tried to get the best out of our players and team to reach the final."
Di Matteo is also reading little into Bayern's 5-2 mauling by Borussia Dortmund in the German Cup final in Berlin last weekend.
Asked to comment on the suggestion that Bayern could be beaten if the attacking threat posed by Franck Ribery and Arjen Robben was nullified, he replied: "I don't think it's as easy or as straightforward as that.
"They have lots of good players," he said. "To be able to win many titles and be competitive in the Champions League and reach the final you need more than two players. You need a good team."
Source: AFP
Source: AFP