City face a tough task to progress in the Champions League after losing the first play-off leg 3-2 to Real Madrid.
Erling Haaland twice put the Blues ahead in a thrilling encounter, but the Spanish side hit back each time, before snatching victory with almost the final kick of the game.
It leaves City needing to win by at least a goal in the second leg to at least level the aggregate scores and have any chance of progressing after a heart-breaking final seven minutes.
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