Pep Guardiola's worst Champions League exits as Barcelona, Bayern Munich & Man City manager - ranked

Guardiola's first season at Bayern Munich was pretty darn good. Despite having to deal with some key absences throughout the year, they romped to the Bundesliga title and also won the DFB-Pokal to clinch a domestic double. However, Guardiola could not replicate Jupp Heynckes' exploits from the previous campaign by adding a Champions League triumph into the mix.

Things started promisingly enough, with Bayern breezing through the group as winners and dispatching of Arsenal in the last 16. A 3-2 aggregate triumph over Manchester United in the quarter-finals then sparked real hopes that they could retain the trophy. However, King Carlo Ancelotti had other ideas.

After Real Madrid eked out a 1-0 win at Santiago Bernabeu, the tie was delicately balanced heading into the second leg. In the return fixture, though, the fatal flaws of Guardiola's style were brutally exposed. First, Sergio Ramos headed in twice from set-pieces, before Cristiano Ronaldo tore Bayern apart on the counter and then struck a free-kick under the wall. 4-0 to Madrid. This one really stung.

After enduring European disappointment during his first season in charge at the Allianz Arena, Guardiola was handed a perfect shot at redemption when Die Roten were drawn against his former club in the semi-finals.

On the eve of the game, Guardiola was dealt a double hammerblow when both Franck Ribery and Arjen Robben were ruled out. For 77 minutes Guardiola seemed to have handled these absences perfectly, reshaping to a 3-5-2 and stifling the infamous MSN frontline.

Most of that positivity disappeared when Lionel Messi popped up with a goal 13 minutes from time, and disappointment turned to disaster when Barca scored twice more before the end to earn a 3-0 victory. The last of these goals - scored on the counter - would not happen today, with Guardiola having urged his charges forward to try and grab an away goal.

Bayern didn't recover in the second leg, although they did win 3-2 on the night. For Guardiola, he had tried to stick one over on his former employers, but he had failed - albeit against a very good team.

Guardiola has never got closer to ending his wait for a third European Cup than in 2021. City's performances on the way to the final were ridiculous, with a goalless group-stage draw against Porto the only thing preventing them from registering a 100 percent winning record over the 12 games.

They also entered the final in Porto as strong favourites, having finished 19 points above Chelsea in the Premier League that season. Guardiola made a big call - continuing his passion for tinkering when the stakes are at their highest - omitting Rodri from his starting XI and also playing without a recognised centre-forward.

City were flat throughout the contest, with Chelsea slipping through in transition just before the break and settling a dull game courtesy of a goal from Kai Havertz. It was a hugely disappointing night for Guardiola. An opportunity to end the all the noise surrounding his Champions League record had slipped away far too easily.

The defining rivalry of Guardiola's third act as a manager has been his duels with Liverpool boss Jurgen Klopp. Domestically, City have had the edge, but the Reds have been the undisputed kings of Europe.

The two leading coaches of their generation squared off in the 2018 Champions League quarter-finals - and it wasn't even close. Mohamed Salah, Alex Oxlade-Chamberlain and Sadio Mane all netted in the first 31 minutes at Anfield, leaving City reeling for the rest of the tie.

They couldn't even win the home leg despite playing extremely well, with Salah and Roberto Firmino cancelling out Gabriel Jesus' early opener to send City crashing out of Europe. It might have been different had Leroy Sane's scrappy goal not been wrongly disallowed on the stroke of half-time, a decision that led to Guardiola talking himself into a red card.

After the dust had settled, the City's boss decision to shoehorn Aymeric Laporte in at left-back against Salah was highlighted as another example of Guardiola's destructive overanalysis.

Jose Mourinho is often viewed as the antithesis of Guardiola and his values. If that's true, Diego Simeone certainly runs him a very close second - and these two contrasting characters were thrown together in the 2015-16 Champions League semi-finals.

Guardiola knew this was his final chance to win the big one before he left Bayern, but his side got off to a nightmare start when Saul Niguez netted the only goal of the first leg after just 11 minutes.Atleti were able to defend their slender lead too, largely thanks to Bayern lacking that killer edge in front of goal.

It was one-way traffic in the return fixture, with Thomas Muller seeing a penalty saved by Jan Oblak, but Die Roten could only score twice, meaning Antoine Griezmann's away goal just after half-time was enough to send El Cholo's ragtag gang of misfits into the final. It felt like a symbolic defeat for Guardiola's possession-heavy style.

Another wildly-dramatic Champions League classic, another defeat for Pep. Son Heung-min settled the first leg, with Guardiola strangely opting to drop Kevin De Bruyne and play Fabian Delph at left-back, but City were far from out of it when they welcomed their opponents to Manchester.

A breathless opening 11 minutes saw the two teams share four goals evenly, before City took control of the tie by netting twice without reply. With Harry Kane injured, the chances of Spurs conjuring a goal to send them through seemed slim.

Step forward Fernando Llorente, a man who likely still haunts Guardiola's dreams. The super-sub was introduced just before half-time after Moussa Sissoko picked up a knock, and he popped up with one of the worst goals of all time to put Spurs on the brink of progressing to the semi-final.

There was to be one final twist, though, with VAR insisting on becoming the main character. Deep into second-half stoppage time, Raheem Sterling thought he'd netted a winner for City, only for his strike to be ruled out for offside after the technology got involved. Guardiola has crashed out of Europe in crazy circumstances before, but this one has to be the most painful.

Barcelona's meeting with Inter in the 2010 Champions League semi-finals was oozing with narrative. This was Mourinho vs Guardiola, a clash of styles, personalities and philosophies. There was also the small matter of Eto'o returning to his former club after being pushed out of the door to facilitate Zlatan Ibrahimovic's arrival.

In the first leg, Inter treated San Siro to a display of counter-attacking excellence. Barca - who started Ibrahimovic despite his and Guardiola's off-field issues - may have taken the lead through Pedro, but strikes from Wesley Sneijder, Maicon and Diego Milito ensured Mourinho's men headed to Camp Nou with a two-goal lead.

What came next was a defensive masterclass, with Inter pulling out every dark trick in the book to book their place in the final. Thiago Motta was sent off early, but Inter were prepared - Mourinho predicted this would happen before the game. When the final whistle went with a 1-0 defeat secured, he enjoyed his crowning moment at the home of the club who turned him down in favour of Guardiola a few years earlier. It was cinematic stuff.

The 2012 Champions League semi-finals pitted Guardiola's all-conquering Barcelona against a Chelsea team fraying at the edges. Roberto Di Matteo was in interim charge of a Blues side well out of the top-four running, and even after he inspired his side to knockout triumphs over Napoli and Benfica, few were expecting his luck to continue against Barca.

But continue it did, as Chelsea converted one of their four shots to earn a smash-and-grab 1-0 victory in the first leg. Barcelona needed to be mentally resolute in the return leg and things seemed to be heading their way after they went 2-0 up.

However, following a familiar pattern, they were done on the counter-attack when Ramires burst through and produced an outstanding lob. That would have been enough to send Chelsea through on away goals, but they made doubly sure of the result in the final seconds, with Fernando Torres adding a second - much to Gary Neville's delight in the commentary booth.

Failing to beat a weakened Chelsea was bad enough. When you consider all this transpired after Blues skipper John Terry had been dismissed before half-time in the second leg, it looks like one of Guardiola's biggest failures.

Starting Isaac Cuenca over the likes of Thiago and Pedro seems bonkers in retrospect, as does the decision in the first leg to sacrifice Gerard Pique when they needed height in the backline to deal with Didier Drogba.

Guardiola's first season in England foreshadowed the European struggles that have plagued his Man City career. The group stage was tougher than expected, with a 4-0 defeat to Barcelona playing a significant role in the Cityzens' second-placed finish.

However, they might have thought they'd found salvation after being drawn against Ligue 1 upstarts Monaco in the round of 16. The first leg was an end-to-end classic, an eight-goal thriller that City edged 5-3.

Despite the entertainment, there was a lingering sense that Guardiola's side had been far to open over the 90 minutes and these cracks of doubts would eventually lead to City's Champions League dreams smashing into a million pieces. Those cracks were realised at the Stade Louis II, as Kylian Mbappe and Fabinho were among the scorers as Monaco progressed thanks to a 3-1 victory.

In the aftermath, Guardiola attracted rightful criticism. Before the second leg, he had vowed to attack the French side from the off, but this gung-ho style left them vulnerable and ultimately led to their elimination. In this case, Guardiola had transparently opted for style over results.

Played inside an empty stadium in Lisbon due to the pandemic, City's elimination in 2020 made for bizarre viewing. It wasn't just the lack of crowd noise that created this uneasy atmosphere, though. It was also strange to witness Guardiola's charges crumble against such modest opposition.

When the 2019-20 Ligue 1 season was curtailed, Lyon were sat in seventh place, 28 points off leaders Paris Saint-Germain and nine points outside the top four. They'd also not played for months due to the French domestic campaign not resuming, unlike the Premier League. This was as easy as it gets for City, surely? Not quite.

Shambolic defending gifted Maxwel Cornet the opener and City were equally porous to allow Moussa Dembele to make it 2-1 11 minutes from time. Sterling would then miss an absolute sitter before Dembele sealed the win by capitalising on a terrible Ederson error.

As with a lot of Covid football, it's easy to forgot how poor City were on the night, but it has to go down as one of Guardiola's lowest points in the Champions League. His team selection was strange. Eric Garcia was drafted into a back three and had a stinker, while Phil Foden was left on the bench entirely. City only got going when they reverted to a 4-2-3-1 in the second half, with the tactical changes clearly unsettling their momentum.

As collapses go, this was absolutely spectacular. After a first-leg slobberknocker which City just edged 4-3 at the Etihad, Madrid needed a strong start in the return game to have any chance of reaching the final.

It did not come and they laboured through proceedings until Riyad Mahrez seemingly dumped them out of the competition by netting a stunning goal 18 minutes from time. That should have been that, but this was a Guardiola team in Europe, so of course they managed to find a way to blow it.

Two Rodrygo goals in just over a minute right at the death sent the game to extra-time, and it was painfully evident City did not have the mental fortitude to recover from such a blow. Right on cue, Karim Benzema was lazily brought down by Ruben Dias in the box and the Frenchman tucked away his penalty with aplomb. If ever a game summed up the footballing gods being against Guardiola, this was it.

All his side had to do was defend their box for less than 20 minutes. But the fear kicked in and Madrid kicked them out of Europe.