Manchester City is on the eve of a historic quadruple, but Pep Guardiola will have to break new ground to continue their quest on Wednesday evening.
After three consecutive semifinal defeats of the Champions League in Bayern Munich, he has been unable to get hold of City after the last eight since his arrival in 2016.
He didn't even reach the final because his iconic Barcelona side had destroyed Manchester United in 2011. Sportsmail looking back on his six European exits since …
Barcelona 2-3 Chelsea (semi-final)
Pep Guardiola has not reached 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 home
|Season||Date||Team||Opponent||In front of||Against||Place||Result||Round|
|2013/14||23/04/2014||Bayern Munich||Real Madrid||0||1||A||L.||Semi finals|
|2013/14||29/04/2014||Bayern Munich||Real Madrid||0||4||H||L.||Semi finals|
|2014/15||2015/06/05||Bayern Munich||Barcelona||0||3||A||L.||Semi finals|
|2014/15||2015/12/05||Bayern Munich||Barcelona||3||2||H||w||Semi finals|
|2015/16||27/04/2016||Bayern Munich||Atletico Madrid||0||1||A||L.||Semi finals|
|2015/16||2016/03/05||Bayern Munich||Atletico Madrid||2||1||H||w||Semi finals|
|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||2018/04/04||Manchester City||Liverpool||0||3||A||L.||Quarter final|
|2017/18||2018/10/04||Manchester City||Liverpool||1||2||H||L.||Quarter final|
Pep Guardiola had announced his intention to stand in Barcelona in the summer of 2012, and this was his chance to draw in style.
No manager had yet to successfully defend the Champions League, but if someone were to do it, it would certainly be Pep and his wonderful Barca party at their peak.
They were heavy favorites against Chelsea, led by caretaker Roberto Di Matteo. But the winner of Didier Drogba at Stamford Bridge gave them a first leg advantage.
Barcelona flew out of the traps in the Nou Camp. Sergio Busquets and Andres Iniesta both scored on a red card by John Terry.
But it disintegrated when Ramires' stunning goal placed it in Chelsea & # 39; s advantage before that goal of Fernando Torres confirmed their passage with only 28 percent of the ball in the time of interruption.
Bayern Munich 0-5 Real Madrid (semi-final)
Guardiola looks bleak, while Bayern Munich is blown away by Real Madrid in the 2014 semi-final
Sergio Ramos scored two first half headers as Real riots ran on the Allianz in the second leg
Two years after the Chelsea debacle, Guardiola was back in its natural habitat, this time with Bayern Munich after taking a sabbatical.
Bayern were the holders but came across a rampant Real Madrid side under the European specialist Carlo Ancelotti.
The goal of Karim Benzema was the difference after the first leg at the Bernabeu, but Bayern had to increase the pressure in the Allianz Arena.
Instead, they were torn apart. Sergio Ramos scored two headers in the first 20 minutes and Cristiano Ronaldo made three before half time.
With the game everything but Ronaldo added another for the final whistle to add to the misery of Pep.
Bayern Munich 3-5 Barcelona (semi-finals)
It was an unfortunate return to Barcelona for Guardiola with Bayern Munich in 2015
Lionel Messi lifts the ball over Manuel Neuer and Barcelona beats Bayern Munich 3-0
Three years after his emotional departure from Barcelona, Guardiola finally got his homecoming.
Luis Enrique's side was a different beast than his tiki-taka miracles, but he still had to fight against Lionel Messi.
It went so well in the preliminary round at the Nou Camp until the last quarter when Messi defeated Manuel Neuer for power from the edge of the area.
His second was a magical one when he got up on Jerome Boateng, saw him fall to the ground and then lifted the ball over Neuer. Neymar ran away to make it 3-0.
A 3-2 victory in the way back was unimportant, the damage had already been done.
Bayern Munich 2-2 (A) Atletico Madrid (semi-final)
Guardiola & # 39; s dream of a third Champions League derailed by Atletico Madrid in 2016
Antoine Griezmann scored the crucial away game for Atletico Madrid in the second leg
Pep Guardiola was already announced as the next boss of Manchester City. And this was his chance to get a high card and eventually deliver the Champions League to Munich.
Saul Niguez's solo goal gave Diego Simeone the lead on a finely balanced second leg in the Allianz.
Xabi Alonso's deflected free kick halted the equalizer for halftime, but fate struck when Antoine Griezmann was cleared by Fernando Torres and moved past Neuer.
Robert Lewandowski's header set a hectic final, but Bayern was unable to secure a decisive third place and left goals that Pep & # 39; s legacy left incomplete.
Manchester City 6-6 (A) Monaco (last 16)
Guardiola & # 39; s Manchester City was upset by Monaco in 2017 in an exciting two-legged tie
Tiemoue Bakayoko scored the decisive away game when Monaco passed City in the last 16
Monaco felt like a favorable draw for Manchester City in the last 16 of the Champions League in 2017. That prediction could not have been more wrong.
An extraordinary first stage on the Etihad ended with 5-3 on the hosts, but that doesn't even come close to telling the whole story.
The young indictments of Leonardo Jardim were about to make their way to an unlikely Ligue 1 title and this game announced a certain Kylian Mbappe.
Radamel Falcao scored twice, including a great chip, but also missed a penalty because late goals from John Stones and Leroy Sane City resulted in a two-goal advantage.
Sane & # 39; s strike 20 minutes after time on the return trip seemed to be enough for City after early strikes from Mbappe and Fabinho.
But Tiemoue Bakayoko went over as a decisive third late in the game when Monaco moved on to goals in the final four.
Manchester City 1-5 Liverpool (quarterfinals)
Guardiola lost his rag when City in Liverpool was blown away by two legs in 2018
Liverpool cut through City in the first leg at Anfield for a 2-1 win in the return fit
Guardiola & # 39; s second season in City was an unthinkable triumph, but again he didn't get stuck in Europe, this time in the Battle of Britain.
Jurgen Klopp's Liverpool had found cracks in their armor during a competition fight at Anfield just a few months earlier. The cracks became open when they were blown away by 3-0 in the first leg.
A quick start was needed in the return and they got it when Gabriel Jesus set them on fire in the second minute.
But Guardiola, furious with arbitrary decisions that went against him, launched a dirty tirade to the officials halfway through and was promptly sent to the stands.
Mohamed Salah extinguished every hope with the indispensable swipe goal the hour before Roberto Firmino booked a stunning victory for Liverpool.