Pep Guardiola’s long wait to reclaim the Champions League will have to go on at least another year after his Manchester City side were dumped out of the semifinals in spectacular fashion by Real Madrid on Wednesday.

After winning the first leg 4-3 at the Etihad, a further goal from Riyad Mahrez at the Bernabeu had City two goals ahead on aggregate and cruising as the second leg ticked over into the final minute. The deed was done. The battle was over. The final beckoned.

But, somehow, City then conspire to concede two goals beyond the 90th minute and another in extra time to lose 3-1 and succumb to one of the Champions League’s most humiliating late collapses. City’s advantage was obliterated when Rodrygo scored twice in the first two minutes of stoppage time before a resurgent Real completed their comeback with a 95th-minute penalty from Karim Benzema — the prolific striker’s 15th goal in Europe this season.

Los Blancos will now face Liverpool in the 2021-22 Champions League final in Paris at the end of the month, while Guardiola will doubtlessly be spending the intervening weeks desperately attempting to analyse how his side managed to pilfer defeat from the jaws of victory in such maddening fashion.

It’s now been 11 long years since Guardiola last experienced Champions League success with his all-conquering Barcelona ensemble of 2010-11, who comfortably saw off Manchester United in the final to lift the trophy.

Controlling almost every aspect of the game from start to finish, Guardiola’s fearsome line-up strolled to a 3-1 victory at Wembley that left Sir Alex Ferguson openly marvelling at the majesty of his opponents in the aftermath. The goals came from Pedro, Lionel Messi and David Villa and were in turn assisted by Xavi, Andres Iniesta and Sergio Busquets.

No manager has suffered more eliminations at the semifinal stage of the tournament during his career than the Spaniard, who has now gone out on six occasions after reaching the final four. The only coach to match this undesirable competition record is his erstwhile foe, Jose Mourinho.

Here we rank each of the times that Guardiola has fallen short in UEFA’s elite club competition over the decade of near-misses and non-starters that has followed since he last lifted the trophy.

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10. 2016-17 round of 16: Manchester City 6-6 AS Monaco (Monaco win on away goals)

Guardiola took on a mass rebuild job at the Etihad and, alas, the knockout phase of the Champions League appeared to come too soon in his first season in charge of Man City, who were knocked out on away goals by Monaco in the round of 16. City came from behind twice to win the first leg 5-3 at home, but their defensive frailties were laid bare as their manager took on an agitated demeanour on the touchlines. Sure enough, those same flaws were exploited repeatedly in the second leg which Monaco — spearheaded by teenage prodigy Kylian Mbappe — won 3-1 to go through on away goals and thus consign Guardiola to the earliest Champions League exit of his managerial career. Just to rub yet more salt into the wound, 2016-17 was also the first season of Pep’s managerial career to end without a trophy.

9. 2019-20 quarterfinals: Manchester City 1-3 Lyon

The 2019-20 campaign saw all Champions League ties from the quarterfinals onwards reduced to single-leg knockout games in order to minimise travel and risk during the height of the COVID-19 pandemic. Still, this didn’t play into City’s hands as Guardiola’s team slumped to a dire 3-1 defeat against French side Lyon behind closed doors at a neutral venue in Lisbon. The game was level at 1-1 in the 79th minute but a couple of decisively slap-dash defensive errors allowed substitute Moussa Dembele to score two goals in the final 10 minutes of the game to settle things in Lyon’s favour. Guardiola was criticised for his overwrought system in the aftermath, particularly his decisions to opt for a back three while also leaving attacking players like David Silva, Bernardo Silva and Mahrez on the bench.

8. 2013-14 semifinals: (Bayern Munich 0-5 Real Madrid)

After a burned-out Guardiola left Barcelona at the end of the 2012-13 season, he returned to the dugout at Bayern feeling suitably refreshed and re-invigorated after his sabbatical. Guardiola took over from Jupp Heynckes, who had led Bayern to Champions League glory the previous year, but he was unable to defend the crown as the Bavarians were unceremoniously dumped out in the semis by Real Madrid. Bayern lost 5-0 on aggregate, a disappointing result compounded by a 4-0 drubbing suffered at home in the second leg as the attack-minded German giants struggle to adjust to their new manager’s patient, possession-based tactics.

7. 2014-15 semifinals: Bayern Munich 3-5 Barcelona

In his second season as Bayern coach, Guardiola suffered the dual ignominy of not only being eliminated in successive Champions League semifinals but also being well and truly schooled by his former team. Still practising their ex-manager’s tactical blueprint, the Catalans scored three late goals to blaze into a 3-0 aggregate lead after the first leg at Camp Nou — a game best remembered for Messi causing Jerome Boateng to crumble into a heap in the build-up to his second goal. Bayern then salvaged some pride by fighting back to win the second leg 3-2 at the Allianz but it wasn’t enough to overcome their opponents and prevent them from reaching their first final, and lifting another trophy, since Pep’s side in 2011.

6. 2015-16 semifinals: Bayern Munich 2-2 Atletico Madrid (Atletico win on away goals)

Guardiola’s third and final season at Bayern — a club where he won seven trophies, including three Bundesliga titles — ended in much the same vein on the European front as Bayern once again suffered the exasperation of falling at the penultimate hurdle. Atletico Madrid scrapped to a 1-0 win in the first leg in Spain and then just about held firm in the fractious return fixture, losing 2-1 to Bayern but advancing on away goals on a night in which both sides missed penalties.

5. 2021-22 semifinals: Manchester City 6-5 Real Madrid

City’s late capitulation in the Spanish capital will be what sticks in the memory, but the damage was really done in the first leg when they scored four goals but also missed a host of other chances that could have ended the tie as a contest at the Etihad. However, Madrid were somehow able to stay in the tie and ended up making their opponents pay. While this exit will be galling for City fans, Madrid had already mounted stunning comebacks against Paris Saint-Germain and Chelsea in this season’s knockout phase, and that air of inevitability surrounding Carlo Ancelotti’s side was not totally dispelled even when Mahrez scored at the Bernabeu. Bowing out to yet another chaotic flurry of goals is tough, but we suspect — for Pep at least — that the waiting is the hardest part. All 11 years of it.

4. 2011-12 semifinals: Barcelona 2-3 Chelsea

Hailed as one of the greatest teams of all time, Barca were heavily tipped to be the first team to win back-to-back European Cups in more than two decades, but the defending champions came unstuck against Chelsea in the semis. With a 1-0 edge to protect from the first leg, the Blues spent vast swathes of the second leg sat deep while defending for their lives at Camp Nou after John Terry was sent off near the end of the first half. Roared on by the 95,000-strong home crowd, the Catalans had a 2-1 lead as the game entered its latter stages and continued to lay siege to the Chelsea goal in search of a vital third that would negate the visitors’ away goal advantage. Then, cometh the 92nd minute, cometh Fernando Torres. The striker was played through one-vs.-one with goalkeeper Victor Valdes, who he dribbled around with ease to roll the ball into the empty net and assure Chelsea of their place in the final.

3. 2018-19 quarterfinals: Manchester City 4-4 Tottenham Hotspur (Tottenham win on away goals)

This exit was especially galling as it was against a fellow Premier League side, and one they had beaten on each of their previous three meetings, too. Spurs won the first leg at their brand-new stadium via a single Son Heung-Min goal which ultimately proved vital after City came back to win 4-3 in a thrilling match at the Etihad. All the old foibles once again combined to undermine City’s efforts as a disappointing first-leg result and repeated defensive inconsistency saw them unable to progress. Even then, Guardiola’s side thought they had pulled off the most frenetic comeback in stoppage time when Raheem Sterling‘s 94th-minute “winner” sent the entire stadium into raptures, only for it to be disallowed for the tightest of offside calls by VAR.

2. 2017-18 quarterfinals: Manchester City 1-5 Liverpool

With his first trophy at City — the Carabao Cup — now in the bag and with the Premier League set to follow, City looked well-equipped to go on a deep European run in 2017-18 only to come unstuck against eventual finalists Liverpool. Electric from the very start, Jurgen Klopp’s team steamrollered to a 3-0 win in the first leg amid a hostile Anfield atmosphere, with all three goals coming within the first half an hour. An unorthodox 3-3-1-3 formation appeared to produce immediate results when City took the lead in the first two minutes of the second leg at the Etihad. However all momentum was lost shortly before half-time when a contentious decision to disallow a Leroy Sane goal for offside saw Guardiola shown a red card for his remonstrations, during which he stampeded out on to the pitch and wagged an accusatory finger at the officials. With their head coach watching on mournfully from the stands, City lost their zeal and Liverpool scored twice in the second half to rack up a hefty 5-1 aggregate thrashing over their league rivals.

1. 2020-21 final: Manchester City 0-1 Chelsea

The closest City have ever come to lifting the Champions League saw Guardiola reach his first final in a decade, where he was pitted against Thomas Tuchel’s Chelsea in Porto. Eyebrows were raised when the teams were released an hour before kick-off and Guardiola had named what appeared to be an extremely attacking lineup: Sterling, Mahrez, Kevin De Bruyne, Phil Foden and Bernardo Silva were all in the XI, while even the presence of Ilkay Gundogan was not by no means the most defensive-minded option in the matchday squad. The winning goal came when Mason Mount‘s pass split the midfield and defence, allowing Kai Havertz to scamper through on goal with virtually the whole City half to himself, nip the ball around the onrushing Ederson and win Chelsea their second European crown just four months after Tuchel had been hired. For Pep, the agony of coming within touching distance of that elusive silverware was almost too much to bear.

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