Di Matteo took over as caretaker boss following the sacking of Andre Villas-Boas in March and promptly led the team on a dramatic run all the way to Saturday's final of Europe's top club competition.
However, although victory over Bayern Munich at the Allianz Arena would earn Chelsea – and Russian oil billionaire Abramovich – a spectacular influx of cash, he still could find himself out of work in the summer.
A senior Chelsea source replied "about 160 million pounds" ($254.7 million) when asked by Yahoo! Sports in a telephone conversation what the estimated financial benefit of a Champions League triumph would be. That amount represents several factors, including the increased value of the Chelsea brand, prize money and associated merchandising sales.
Another crucial factor is that only by beating Bayern would Chelsea get back into the Champions League again next season. Chelsea finished just sixth in the English Premier League, and only the top four EPL finishers qualify for the following season's Champions League. However, if a team outside the top four wins the European tournament, it is granted an automatic spot.
It is that poor league form that has hurt Di Matteo's chances of being named manager on a permanent basis. Yahoo! Sports wrote in early April that lifting the trophy would be enough to guarantee Di Matteo at least a one-year contract, and that information was true at the time.
But Abramovich since has reconsidered, influenced heavily by disappointing recent league results. The source confirmed that defeats to Liverpool and Newcastle, and a scoreless draw against Arsenal in particular, swayed the owner's opinion. That stance may be a little harsh given that a Champions League semifinal victory against Barcelona and the FA Cup final success over Liverpool were interspersed, although those league blips did effectively extinguish any top-four aspirations.
"Roberto could be in the frame, but he won't be guaranteed anything, whatever happens in Munich," said the source. "A lot can happen over the summer."
It now appears Abramovich will analyze the best available names once the season draws to a close. But when it comes to soccer, Chelsea and big money targets, "available" is a relative concept. Figures like Joachim Loew of the German national team may be on the market, but the owner also would not be afraid to buy a big name out of his current contract, like he did with Villas-Boas.
If Di Matteo wins the Champions League, obligation would suggest that Abramovich at least should have him as part of the short list. If Bayern, a strong favorite and playing in its own stadium, prevails, then Abramovich will be on his way, albeit having increased his reputation greatly since stepping into the temporary role. Lazio, of Italy's Serie A, would be one potential suitor.
After the final day of the EPL campaign, Di Matteo was asked if a return to West Bromwich Albion, where he was sacked in February 2011 after 18 mixed months in charge. West Brom is without a chief after Roy Hodgson departed to take over the England national team.
"In my life I have gone back to an ex-girlfriend, and it didn't work out," Di Matteo said. "I'm not sure it would be the right move."
Di Matteo clearly has retained his sense of humor ahead of the biggest game of his managerial career. He may need it again in the summer, whatever Saturday's result.
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