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
| Season | Date | Team | Opponent | For | Against | Venue | Result | Round |
|---|---|---|---|---|---|---|---|---|
| 2011/12 | 18/04/2012 | Barcelona | Chelsea | 0 | 1 | A | L | Semi-Final |
| 2011/12 | 24/04/2012 | Barcelona | Chelsea | 2 | 2 | H | D | Semi-Final |
| 2013/14 | 23/04/2014 | Bayern Munich | Real Madrid | 0 | 1 | A | L | Semi-Final |
| 2013/14 | 29/04/2014 | Bayern Munich | Real Madrid | 0 | 4 | H | L | Semi-Final |
| 2014/15 | 06/05/2015 | Bayern Munich | Barcelona | 0 | 3 | A | L | Semi-Final |
| 2014/15 | 12/05/2015 | Bayern Munich | Barcelona | 3 | 2 | H | W | Semi-Final |
| 2015/16 | 27/04/2016 | Bayern Munich | Atletico Madrid | 0 | 1 | A | L | Semi-Final |
| 2015/16 | 03/05/2016 | Bayern Munich | Atletico Madrid | 2 | 1 | H | W | Semi-Final |
| 2016/17 | 21/02/2017 | Manchester City | Monaco | 5 | 3 | H | W | Last 16 |
| 2016/17 | 15/03/2017 | Manchester City | Monaco | 1 | 3 | A | L | Last 16 |
| 2017/18 | 04/04/2018 | Manchester City | Liverpool | 0 | 3 | A | L | Quarter Final |
| 2017/18 | 10/04/2018 | Manchester City | Liverpool | 1 | 2 | H | L | Quarter Final |
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
Bayern Munich 3-5 Barcelona (semi-finals)
It was an unhappy return to Barcelona for Guardiola with Bayern Munich in 2015
Lionel Messi lifts the ball over Manuel Neuer as Barcelona thrashed Bayern Munich 3-0
Three years after his emotional departure from Barcelona, Guardiola was finally granted his homecoming.
Luis Enrique’s side were a different beast to his tiki-taka wonders, but he still had to contend with Lionel Messi.
It was going so well in the first leg at the Nou Camp until the final quarter when Messi beat Manuel Neuer for power from the edge of the area.
His second was a thing of beauty as he stood up Jerome Boateng, watched him fall to the floor and then lifted the ball over Neuer. Neymar raced away to make it 3-0.
A 3-2 win in the return leg was inconsequential, the damage had been done.
2015-16
Bayern Munich 2-2 (A) Atletico Madrid (semi-finals)
Guardiola’s dream of a third Champions League was derailed by Atletico Madrid in 2016
Antoine Griezmann scored the crucial away goal for Atletico Madrid in the second leg
Pep Guardiola had already been announced as the next Manchester City boss. And this was his chance to sign off on a high and finally deliver the Champions League to Munich.
Saul Niguez’s solo goal gave Diego Simeone’s side the advantage ahead of a finely-poised second leg at the Allianz.
Xabi Alonso’s deflected free-kick leveled the tie before half-time, but disaster struck as Antoine Griezmann was sent clear by Fernando Torres and coolly slotted past Neuer.
Robert Lewandowski’s header set up a frantic finale, but Bayern were unable to muster a decisive third and exited on away goals leaving Pep’s legacy incomplete.
2016-17
Manchester City 6-6 (A) Monaco (last-16)
Guardiola’s Manchester City were upset by Monaco in a thrilling two-legged tie in 2017
Tiemoue Bakayoko score the decisive away goal as Monaco edged past City in the last-16
Monaco felt like a favourable tie for Manchester City in the last-16 of the Champions League in 2017. That forecast could not have been more wrong.
An extraordinary first leg at the Etihad finished 5-3 to the hosts, but that does not even come close to telling the full story.
Leonardo Jardim’s young charges were about to storm their way to an unlikely Ligue 1 title and this game announced a certain Kylian Mbappe to the world.
Radamel Falcao scored twice, including a delightful chip, but also missed a penalty as late goals from John Stones and Leroy Sane gave City a two-goal advantage.
Sane’s strike 20 minutes from time in the return leg looked to be enough for City after early strikes from Mbappe and Fabinho.
But Tiemoue Bakayoko headed home a decisive third late in the game as Monaco progressed on away goals en route to the final four.
2017-18
Manchester City 1-5 Liverpool (quarter-finals)
Guardiola lost his rag as City were blown away by Liverpool over two legs in 2018
Liverpool sliced through City in the first-leg at Anfield before a 2-1 win in the return fixture
Guardiola’s second season at City was an unimaginable triumph, but once again he came unstuck in Europe, this time in the Battle of Britain.
Jurgen Klopp’s Liverpool had found chinks in their armour during a league clash at Anfield just a few months earlier. Those chinks became open wounds as they were blown away 3-0 in the first leg.
A fast start was needed in the return, and they got it as Gabriel Jesus fired them ahead in just the second minute.
But Guardiola, furious at refereeing decisions going against him, launched into a foul-mouthed tirade at the officials at half-time and was promptly sent to the stands.
Mohamed Salah extinguished any hopes with the vital away goal on the hour mark before Roberto Firmino wrapped up a stunning win for Liverpool.