Manchester City stand on the brink of a historic quadruple, but Pep Guardiola will have to break new ground if he is to continue their quest on Wednesday night.
After three successive Champions League semi-final defeats at Bayern Munich, he has been unable to get City past the last eight since arriving in 2016.
He has even failed to reach the final since his iconic Barcelona side swatted aside Manchester United in 2011. Sportsmail look back at his six European exits since...
2011-12
Barcelona 2-3 Chelsea (semi-finals)
Pep Guardiola has failed to reach the final of the Champions League since 2011
Chelsea came from 2-1 and a man down in the 2012 semi-final to shock Barcelona at home
Pep Guardiola had signaled his intention to stand down at Barcelona in the summer of 2012, and this was his chance to sign off in style.
No manager had yet to successfully defend the Champions League but if anyone was going to do it, it would surely be Pep and his resplendent Barca side at their peak.
They were heavy favourites against Chelsea, led by caretaker Roberto Di Matteo. But Didier Drogba's winner at Stamford Bridge gave them a first leg advantage.
Barcelona flew out of the traps at the Nou Camp. Sergio Busquets and Andres Iniesta scored, either side of a John Terry red card.
But it fell apart as Ramires' stunning away goal put it back in Chelsea's favour on the stroke of half-time, before THAT Fernando Torres goal in stoppage time confirmed their passage through with just 28 per cent of possession.
2013-14
Bayern Munich 0-5 Real Madrid (semi-finals)
Guardiola looks glum as Bayern Munich are blow away by Real Madrid in the semi-finals in 2014
Sergio Ramos scored two first-half headers as Real ran riot at the Allianz in the second leg
Two years after the Chelsea debacle Guardiola was back in his natural habitat, this time with Bayern Munich after taking a sabbatical.
Bayern were the holders but ran into a rampant Real Madrid side under European specialist Carlo Ancelotti.
Karim Benzema's goal was the difference after the first leg at the Bernabeu, but Bayern were expected to crank up the pressure at the Allianz Arena.
Instead they were mauled. Sergio Ramos scored two headers in the first 20 minutes and Cristiano Ronaldo made it three before half-time.
With the game all but over Ronaldo added another before the final whistle to add to Pep's misery.
2014-15
