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Every Pep Guardiola Champions League exit since last triumph in 2011

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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.

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.

Pep Guardiola had already been announced as the next Manchester City boss.

Saul Niguez's solo goal gave Diego Simeone's side the advantage ahead of a finely-poised second leg at the Allianz.

Monaco felt like a favourable tie for Manchester City in the last-16 of the Champions League in 2017.

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.

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