Pep Gaurdiola side Manchester City are out of the UEFA Champions League after AS Monaco struck late to seal a stunning away-goals victory, which ended 6-6 on aggregate.
Manchester City were 13 minutes from a place in the top-8 after clawing themselves back into a second leg their hosts had dominated, but slack marking from a set-piece allowed defender Tiemoue Bakayoko to head home the decisive goal.
Having won the competition two times in his era at Spanish team Barcelona, this in the first time in manager Pep Gaurdiola's career that he has gone out at this stage.
Leonardo Jaordim side lost 5-3 in an extraordinary first leg in Manchester City but dominated the first half at the Stade Louis 2 and opened the netting through the brilliant 18 years old striker Kylian Mbappe's poked finish from close range.
The French league side, who had netted 123 goals so far this season, deservedly doubled their advantage on the night, punishing the visitors sluggish start through defender Fabinho's crisp strike.
The English side failed to muster any sort of shot in the opening 45 minutes and it took until the 65th minute for Argentine striker Sergio Aguero to call goalkeeper Daniel Subasic into a sharp save.
They forced their way into the match-and back into the aggregate lead-as winger Leroy Sane swept in when Subasic parried midfielder Raheem Sterling's low strike, but their defence could not hold out.