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Real Madrid advanced to the semifinals of the Champions League after beating Manchester 4-3 on penalties at City of Manchester Stadium on Thursday morning (AEDT).
Antonio Rudiger struck the decisive spot kick after the game had finished 1-1 through extra time and 4-4 on aggregate.
Bernardo Silva and Mateo Kovacic both saw their penalties saved in the shootout as defending champion City was eliminated by record 14-time winner Madrid.
Rodrygo fired Madrid ahead in the 12th minute with a twice-taken effort from close range to beat City goalkeeper Ederson on the rebound.
City dominated the game from then on with Kevin De Bruyne levelling in the 76th by lifting a shot high into the net from close range.
The match was tied 4-4 on aggregate after the first leg ended 3-3 in Madrid last week.
City immediately took advantage in the shootout after Julian Alvarez converted his opening penalty and Luka Modric's effort was saved.
But Madrid keeper Andriy Lunin then saved successive spot kicks from Silva and Kovacic to swing the balance in the visitors' favour.
Defeat ended City's bid to become the first English team to win back-to-back Champions League titles and its pursuit of successive trebles. City is still challenging for the Premier League title and FA Cup.
Victory for Madrid keeps the Spanish giant in the hunt for a record-extending 15th European Cup. It also saw it advance to the semifinals for the fourth year in a row — denying City the chance to emulate that feat.
But Madrid had to dig in to get past Pep Guardiola's team, which dominated the majority of the match without managing to add to De Bruyne's second-half goal.
"I have to say thank you to these players from deep in my heart because the way they played. But football is about winning and we didn't do enough yet we were exceptional," Guardiola said after the match.
"Sometimes you can win on penalties and sometimes you cannot. But in the game we did not convert the chances that we had, even though we defended really well. Everyone performed at a high level. We said we would have to be at our best to play Real Madrid and they were.
"I would have preferred to have won but congratulations to Real Madrid. We did everything so I have absolutely no regret about anything we have done.
"I always say as a manager, it is about scoring more and conceding less and we did everything. We played exceptional but unfortunately we could not win so it is what it is"
Bayern Munich could yet crown a disappointing season with the Champions League title as Arsenal faces the prospect of ending a promising season with no trophy.
Joshua Kimmich's header powered Bayern to a 1-0 win over Arsenal to reach the Champions League semifinals with a 3-2 victory on aggregate.
With the score at 2-2 from the first leg in London, Kimmich's header off Raphael Guerreiro's pinpoint cross put Bayern ahead in the 63rd minute as Bayern largely neutralised the English team's attack.
Arsenal's players were "gutted," manager Mikel Arteta told broadcaster TNT Sports.
"I cannot find the right words to lift them," he said.
Bayern kept alive its hopes of finishing the season with a trophy three days after Bayer Leverkusen ended Bayern's 11-year reign as German champion.
Striker Harry Kane — who spoke on Tuesday of being motivated by his release from Arsenal as a youth player — takes a step closer to what would be the first trophy of his career.
Thomas Tuchel said it meant "really a lot" to beat Arsenal.
"The semifinals are an important step, the last four, that was fun," he said.
Bayern and Arsenal have been drawn together five times in the knockout stages of the Champions League since 2005 and the German team has eliminated Arsenal on each occasion.
Arsenal's Champions League exit follows a heavy blow to its Premier League title ambitions in a 2-0 loss to Aston Villa on Monday. Defeat also rules Arsenal out of next year's Club World Cup in the United States, in favour of Austrian team Salzburg.
Arsenal was left to rue the defensive errors that cost the team in the first leg.
"We gave them two goals, a big advantage to give away, and today you could see it was margin of error zero, we made a mistake defending the goal and we conceded," Arteta said.
"Then it was difficult. We tried in many different ways but it's difficult. It is the moment to stay next to the players, give them support, because they are the ones who have taken us on this journey."
AP
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