For the second time in Abramovich's nine years as owner, Chelsea will contest the most important club game on the planet.
The lure of the Champions League is what brought the Russian billionaire to Stamford Bridge, his hunger to win it has arguably cost half a dozen managers their jobs.
Now Di Matteo finds himself in the bizarre position of knowing victory over Bayern Munich may not save him the axe either.
But he hopes, as do all those wearing blue who will cheer on the club Roman built, the journey will reach its end in the Allianz Arena, living in the absolutely certainty that one day Abramovich's dreams will be realised.
"We can win it," said Di Matteo.
"We have to believe and have the confidence to do so.
"I don't know how somebody else feels. I can only guess he (Abramovich) is excited.
"Sooner or later it will come.
"We hope it's tomorrow [Saturday]. But with the quality that's been at this club before and will certainly come into this club again, it will happen."
The 68th richest person in the world, according to Forbes, Abramovich's Champions League history is scarred by ill fortune.
Luis Garcia's ghost goal for Liverpool in 2005, John Terry slipping as he lined up the penalty that would have secured victory over Manchester United in 2008, Andres Iniesta scoring a semi-final winner for Barcelona in injury-time 12 months later.
No amount of money can ease the pain of being kept apart from that elusive prize.
"I haven't had direct message from the owner," said Frank Lampard.
"The general message is always there.
"He has put a lot into this club. Without him, we wouldn't be sitting here now.
"He's always been behind us. You don't get into a final very often. We want to win it now."
Di Matteo cannot afford to get sucked into the emotion.
"You make your own destiny and fate," he said.
"Reaching the last stages of this competition is difficult enough and you always need a bit of luck in a cup competition."
Chelsea's fortune came in the acceptance of Di Matteo to take charge on an interim basis following the dismissal of Andre Villas-Boas at the beginning of March.
It has been suggested that the decision to make a change followed expressions of discontent from senior players.
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"People think that we ring up the owner now and again and decide who comes and who'll be sacked," said Lampard.
"That's not how it works at this club. It shouldn't be like that at any club.
"A decision like that is taken out of your hands."
However the conclusion was reached, it worked.
Chelsea are reliant on winning tomorrow's [Saturday's] game in order to qualify for next season's Champions League.
The mere fact they have that chance, having lifted the FA Cup a fortnight ago, is confirmation Di Matteo not only stabilised the situation but managed to get the Chelsea ship moving forwards again, thanks chiefly to a memorable night against Napoli in a last-16 tie that, under Villas-Boas' watch, appeared to have drifted out of reach.
"We have had a difficult season," said striker Didier Drogba.
"We had a lot of criticism. But when big teams don't perform that is what you expect.
"We've shown everyone that we're still a very good team and, if we win tomorrow [Saturday], everybody will just remember we won the cup."
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Chelsea will have to win it without inspirational skipper John Terry, who is suspended, along with Ramires, Raul Meireles and Branislav Ivanovic.
Thankfully for Di Matteo, David Luiz and Gary Cahill have recovered from their respective hamstring injuries and although Lampard sparked a worry when he did a few stretches during training, the veteran midfielder appeared unconcerned.
So now Di Matteo, who spent six seasons with the Blues as a player, will try to engineer the best day of Abramovich's footballing life and Chelsea's entire history, with Lampard accepting it would have been virtually impossible without the Italian manager.
"You can see his importance in the results," said Lampard.
"Roberto has been very clever managing the situation.
"We were struggling for confidence and rather than come in and make drastic changes, he spoke to everyone individually and created confidence in the group.
"We got wins - the Napoli game changed everything - and from then on quietly he's done a perfect job.
"If anyone deserves to win this game, it's him."