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 Inter Milan and Real Madrid boss Mourinho, who had won three of his previous 15 encounters with Guardiola's Barcelona.
The Spaniard remains his nemesis.