Kevin De Bruyne broke an unwanted record during Manchester City's Champions League exit at the hands of Real Madrid.
Man City had aspirations of completing an historic double-treble this season, but those hopes were crushed on Wednesday when they were knocked out of the Champions League by Real Madrid.
The two sides played out a thrilling 3-3 draw in the first leg of their quarter-final tie last week, and in the return fixture they again couldn't be separated.
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Late in the second half City's midfield maestro Kevin De Bruyne cancelled out Rodrygo's early opener to tie up the aggregate score at 4-4, but the home side failed to make their dominance count.
Over 120 minutes Pep Guardiola's side enjoyed 67 per cent possession, took 33 shots, had 18 corners and recorded an xG rating of 2.74, but they just couldn't find a second goal even though Madrid were there for the taking.
Los Blancos held out for penalties before seizing their moment; after Luka Modric missed his side's opening spot-kick, the visitors scored their next four while Andriy Lunin saved from Bernardo Silva and Mateo Kovacic to secure a 4-3 win.
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Though he scored City's only goal on the night, De Bruyne did not have a good evening.
Aside from smashing a simple late chance over the crossbar that would have put City through, the 32-year-old performed well below his normal level.
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The Belgian's passing and crossing were sub-par, while he proved largely ineffective in a central position that could have been occupied by an in-form Phil Foden.
His sloppiness on the ball is pro
De Bruyne lost possession 37 times before he was substituted in the 112th minute, a record in a Champions League match this season.
City and De Bruyne will have to pick themselves up ahead of Saturday's FA Cup semi-final clash with Chelsea, before turning attention to the Premier League title race.
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Topics: Manchester City, Champions League, Kevin De Bruyne, Real Madrid, Football
Alex Brotherton