da roleta： The Catalan is a two-time Champions League winner, but his relationship with European competition has not always been rosy
da cassino： In 2009, a fresh-faced Pep Guardiola did the unthinkable, winning the Champions League in his first-ever season as manager. Manchester United were Barcelona's victims in the final, with a toe-poke from Samuel Eto'o and a back-post Lionel Messi header seeing the Blaugrana to victory at Stadio Olimpico.
Two years later, Guardiola would lift the famous trophy for a second time as United were again their unfortunate opponents in the final. This time, Barca put on an exhibition, romping to a 3-1 victory thanks to goals from Messi, Pedro and David Villa. At full-time Sir Alex Ferguson conceded that Guardiola's side was the best he had ever faced and it seemed that the European trophies would just keep on flowing for the Catalan.
However, since that fateful night, Guardiola has had 10 attempts to clinch a third Champions League crown and failed every single season. There's been plenty of times throughout the period when it seemed certain that the drought would end, only for his teams to somehow manage to grab defeat from the jaws of victory.
His own overthinking has played a role too, with Guardiola remaining obsessed with adding another European Cup to his bulging trophy collection. Below, GOAL ranks the legendary coach's worst Champions League eliminations as he looks to avoid history repeating itself against Real Madrid on Wednesday…
Getty Images2013-14: Eliminated in semi-final by Real Madrid
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.
AdvertisementGetty Images2014-15: Eliminated in semi-final by Barcelona
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.
Getty Images2020-21: Lost in the final to Chelsea
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.
Getty Images2017-18: Eliminated in quarter-final by Liverpool
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.