Manchester City's hopes of a second treble in a row are now over after Real Madrid beat the Champions League holders on penalties on Wednesday night.
Rodrygo put Los Blancos ahead in the 12th minute, only for Kevin De Bruyne to send the match to extra-time.
With no team unable to score again, the showdown then went to penalties.
City struck first, with Julian Alvarez stepping up, with Ederson then saving from Luka Modric.
Man City star Bernardo Silva missed a penalty in the shootout as Real Madrid knocked the holders out of the Champions League
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However, City immediately missed themselves - with Bernardo Silva sending a tame effort into the hands of Andriy Lunin.
From that moment on, Pep Guardiola's side were unable to get themselves back into it.
Jude Bellingham kept his cool from 12 yards before Lunin made another save to deny former Real star Mateo Kovacic, who had come on for De Bruyne in the closing stages.
Real stalwart Lucas Vazquez struck before Phil Foden scored, with Nacho Fernandez and Ederson then trading blows.
However, former Chelsea star Antonio Rudiger bagged the winning spot-kick to end City's hopes of yet another treble.
For City, this will be a bitter pill to swallow.
They were the better team on the night, managing 33 shots - including nine on target - while having more of the ball and completing more passes.
However, ultimately, it wasn't enough.
City will look at a big miss from De Bruyne towards the end of normal time and rue their failure to kill off Real, with Jack Grealish and Erling Haaland - who was surprisingly subdued - also going close.
Carlo Ancelotti's side have a habit of winning when their backs are against the wall, however, and are now dreaming of a stunning 15th Champions League triumph.
City won't have too long to reflect on their defeat, however.
They're next in action against Chelsea in the semi-finals of the FA Cup on Saturday (5.15pm).
And City will be confident of securing the Premier League title, too, given they're currently two points clear at the top of the table.
Arsenal, their nearest rivals, are starting to crumble under the pressure.
The Gunners exited the Champions League themselves earlier on Wednesday night, with Bayern Munich winning 1-0 at the Allianz Arena following a goal from Joshua Kimmich.
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Real Madrid players celebrate after beating Manchester City in the Champions League on Wednesday night
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Reacting to City's defeat, former England star Paul Robinson said it had been a 'real smash and grab'.
"Real Madrid didn't go away, they defended resolutely," he said.
"Rudiger and Nacho both stepped up and both scored their penalties.
"You feel for this Man City team. A real smash and grab."
He added: "We watched a perfectly executed game plan from Real Madrid."
Real Madrid star Jude Bellingham celebrates with the club's supporters after their dramatic Champions League win over Man City
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There are now no English teams left in the Champions League.
Borussia Dortmund will go up against Paris Saint-Germain in the first Champions League semi-final, with the first leg set to take place on April 30.
Bayern Munich will face Real Madrid on the same night.
