Pep Guardiola will continue his quest to win an elusive Champions League title at Manchester City this week, as the Premier League champions take on RB Leipzig in the second leg of their last-16 tie.

Guardiola rose to prominence with two Champions League successes in three seasons at Barcelona, but has failed to regain his grip on Europe’s top prize since leaving the Spanish superpower more than a decade ago.

Despite managing perennial contenders in Bayern Munich and Manchester City, it’s been a rather chequered modern history on the Champions League stage for Guardiola and he will be keen to avoid another early exit as Leipzig visits the Etihad this week.

Ahead of the clash, we look at six of Pep Guardiola’s worst-ever Champions League fails.

Bayern Munich 0-4 Real Madrid (2013/14)

After a brief sabbatical from the game, Guardiola headed to Bayern Munich ahead of the 2013/14 campaign as the Spaniard inherited the reigning European champions.

Bayern had swept to treble success the previous season and looked on course to defend their Champions League title after easing past Arsenal and Manchester United to reach the last four. Guardiola’s side faced Real Madrid in the semi-final, a side who had been regular rivals to the Spanish coach during his tenure at Barcelona.

Real Madrid arrived in Munich with a 1-0 lead to protect following a tight first leg, but hopes of a fightback from Guardiola’s side were ended on a harrowing evening at the Allianz Arena. The visitors ran riot to thrash Bayern, as Sergio Ramos’ brace of headers and Cristiano Ronaldo’s goal on the counter put Real Madrid 3-0 up at half-time.

Ronaldo’s free-kick added gloss to an emphatic scoreline in Bavaria, as Real Madrid progressed to a first Champions League final since 2002 and ensured Guardiola’s first European campaign with Bayern ended in embarrassment.

Liverpool 3-0 Manchester City (2017/18)

Having collapsed against Monaco during a pulsating tie the previous season, Manchester City again suffered an early exit during Guardiola’s second season at the Etihad.

It was familiar opposition who did the damage, as a first-half blitz saw Liverpool take control of a quarter-final meeting between the Premier League rivals. Jurgen Klopp’s side had inflicted City’s only defeat of the league season to date and repeated the trick after a performance of attacking intensity at a raucous Anfield.

Mohamed Salah opened the scoring from close range after some poor defending from the visitors, before Alex Oxlade-Chamberlain blasted in a second to double the advantage. A shell-shocked City struggled to get to grips with the pressure from their hosts and Sadio Mane made it three before the break after heading home Salah’s cross.

A resounding win for the Reds saw Klopp’s side take control of the tie and Liverpool completed the job with a come-from-behind win at the Etihad in the return. City – who recorded a record 100 points during the domestic season – ended the campaign 25 points clear of their Champions League conquerors in the Premier League.

Manchester City 4-3 Tottenham (2018/19)

Manchester City’s Champions League campaign again ended at the hands of English opponents in 2018/19. Pep Guardiola’s side were in pursuit of an unprecedented quadruple but exited the Champions League at the quarter-final stage following an all-time classic with Spurs.

Son Heung-min’s winner had given Spurs a narrow first-leg lead, before an enthralling end-to-end encounter at the Etihad in the return saw the north Londoners progress on away goals.

A chaotic opening period saw City lead 3-2 after just 21 minutes of action, as fine attacking football and defensive fragility defined an unforgettable contest. Raheem Sterling and Son each scored braces, with Bernardo Silva also on the scoresheet to provide City with the advantage on the night.

Sergio Aguero’s second-half goal put City ahead in the tie, but Fernando Llorente bundled in a third goal for Spurs, awarded after consultation with VAR, to put the visitors back ahead on away goals. There was still time for more drama as Sterling saw a stoppage-time winner for City disallowed for offside, with Spurs progressing following a night of compelling drama.

Manchester City 1-3 Lyon, quarter-final (2020)

Pep Guardiola’s dream of Champions League success with Manchester City again ended in humbling fashion during the 2019/20 season, as underdogs Lyon dumped out the tournament favourites.

In a one-legged quarter-final tie hosted in Lisbon, City were second best to a Lyon side who slumped to a seventh-placed finish in Ligue 1. Maxwel Cornet fired the French side into the lead with a wonderful effort, before Kevin De Bruyne hit back to level after the break.

City, however, were far from their best and Guardiola’s experimentation of a back three system backfired, as the Premier League champions were undone on the break. Moussa Dembele raced away to put Lyon ahead in controversial fashion, with appeals for an offside and foul in the build-up dismissed by VAR.

Raheem Sterling’s astonishing open-goal miss saw City waste a glorious chance to equalise, before Dembele scored a second after capitalising on a mistake from Ederson to secure Lyon’s first Champions League semi-final in a decade.

Meanwhile, City exited the Champions League at the quarter-final stage for a fourth straight season.

Manchester City 0-1 Chelsea (2020/21)

Guardiola’s tactical gamble was again blamed as City endured an agonising near miss in their pursuit of an elusive European title in 2021.

City progressed to a first-ever Champions League final during the 2020/21 campaign and faced Chelsea in an all-Premier League decider in Porto. Guardiola’s decision to start without a recognised defensive midfielder was questioned and it was a selection which backfired as Chelsea claimed a deserved win.

Kai Havertz's first Champions League goal @kaihavertz29 | @ChelseaFC | #UCL pic.twitter.com/cc6TpzflbU

— UEFA Champions League (@ChampionsLeague) June 2, 2021

Kai Havertz scored the decisive goal, as the German raced onto Mason Mount’s through ball to round Ederson and secure a second Champions League title for Chelsea. It was a third consecutive win for Thomas Tuchel against Guardiola, with Chelsea having also beaten City in both the Premier League and FA Cup since his appointment in west London just six months earlier.

City, within touching distance of the trophy, added another disappointment to their European record with Guardiola coming under scrutiny for his part in the club’s final defeat.

Real Madrid 3-1 Manchester City (2021/22)

Manchester City were on course for a second successive final in 2021/22, before a late fightback from Real Madrid led to one of the most remarkable conclusions to a Champions League tie.

A brilliant first leg had seen City take a 4-3 lead to Spain for the return, before Riyad Mahrez’s goal looked to have all-but-secured the visitor’s place in the final. City led by two goals on aggregate heading into the final minute at the Bernabeu, with the home side having failed to muster a single shot on target.

What followed was astonishing, as two goals in 90 seconds from Rodrygo forced extra-time and left City stunned. The Brazilian turned in from Karim Benzema’s centre to give Madrid hope, before heading home Dani Carvajal’s cross moments later to spark wild celebrations from the home crowd. Guardiola’s side were unable to recover from the staggering setback and Karim Benzema’s penalty in the added period sent Real Madrid through.

After comeback wins against PSG and Chelsea in the previous rounds, this was the latest feat of escapism from Real Madrid, who beat Liverpool in the final to win a 14th European crown. City – on the floor as an ecstatic Bernabeu revelled in their side’s triumph – ended on the wrong end of a Champions League semi-final few will forget.

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The post Six of Pep Guardiola’s worst ever Champions League fails first appeared on The Football Faithful.