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 shoot-out 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 a goal 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, teenage substitute Romelu Lukaku saw his effort saved as the Germans claimed a 5-4 shoot-out 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 just three of his previous 15 encounters with Guardiola's Barcelona.
The Spaniard remains his nemesis.
Bayern, treble winners last season and labelled the "perfect" team by Mourinho on the eve of the match, were without influential midfielder Bastian Schweinsteiger due to an ankle injury, but were dominant in an enthralling encounter.
The Blues were on the back foot for most of the evening, but went in front courtesy of a goal on the break.
Restored to start following a striker-less line-up at Manchester United, Torres was at his clinical best in converting Andre Schurrle's cross, showing Mourinho he is prepared to fight new recruit Samuel Eto'o for his place.
Bayern had been torn apart, but they continued to press forward.
Newly crowned European Player of the Year Ribery was Bayern's most threatening player and Chelsea failed to heed the frequent first-half warnings.
Two minutes after the restart the France forward drifted in off the left and fired in an unstoppable 25-yard shot to equalise.
After Ramires' sending-off, Chelsea regrouped and Hazard replicated Ribery's strike, only from closer in, and Petr Cech made a series of fine saves.
Cech could not deny Martinez, though, as the destination of the trophy was determined by spot-kicks.
With nine successful penalties it came down to Lukaku, but his spot-kick was soft and Manuel Neuer made a comfortable save.
Neither Mourinho nor Guardiola were in charge of their respective teams when they won the competitions which brought them to Prague.
Guardiola, following a year's sabbatical after leaving Barcelona, replaced the now retired Jupp Heynckes and Mourinho succeeded Rafael Benitez.
The Blues were seeking to make amends for their appearance in the Super Cup last season, when they were beaten 4-1 by Atletico Madrid in Monaco and made two changes from the 0-0 draw at Old Trafford on Monday, with David Luiz making his first appearance of the season following a hamstring injury alongside Torres.
But it was to be Bayern Munich's night.