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.
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.”
The Champions League final kicks off at 1.45am on Sunday morning, Thai time.