Pep Guardiola's Bayern Munich twice came from behind to beat Jose Mourinho's 10-man Chelsea and win the European Super Cup in a penalty shootout at the Stadion Eden in Prague.
Chelsea thought they had handed Mourinho a first trophy of his second spell as boss when Eden Hazard netted in extra time after Franck Ribery had cancelled out Fernando Torres' opener.
The dismissal of Ramires for a second bookable offence left the Blues exposed and Javi Martinez tucked in with the final kick of an astonishing game, forcing penalties.
The 2012 European Cup final between the sides had been decided on spot-kicks in Chelsea's favour and on this occasion, shooting towards the boisterous Bayern end, 20-year-old substitute Romelu Lukaku saw his effort saved as the Germans claimed a 5-4 shootout success.
It denied Mourinho a first European Super Cup and a maiden trophy of his second spell at Stamford Bridge.
There had also been personal pride at stake for former Internazionale and Real Madrid boss Mourinho, who had won three of his previous 15 encounters with Guardiola's Barcelona. But the Spaniard remains his nemesis.
The Chelsea manager was steadfast in his belief that Chelsea deserved to lift the trophy.“The best team clearly lost the match,” said the Portuguese.
“The best team played with 10 men for a long, long period in the game. They played against the champions of Europe and they were the best team. (But) we have reasons to be proud and to believe in the future.”
Mourinho thought the decision to send off Ramires, who picked up a second booking for a foul on Mario Gotze in the closing stages of the second half, was a touch harsh given the context of the game.
He said: “I'd prefer to say no, even if you say yes. Rules are rules but there is a very important rule which is common sense, which is the passion for the game. When a referee takes this decision, I'm not sure he's in love with football.”
On Torres' performance, Mourinho added: “He's working fantastically since the first day, so I hope he gets confidence in matches like this one. He had a very good match.”
Torres will have competition this season from Samuel Eto'o, who signed for the Stamford Bridge club on a one-year deal on Thursday.
Chelsea have also been linked with Manchester United striker Wayne Rooney but when asked if he plans on strengthening his squad before the transfer deadline day on Monday, Mourinho replied: “No, I don't think so.”