Manchester City's Champions League campaign ended in disappointment as they beat Bayern Munich but finished behind Napoli, who secured the win they needed against Villarreal.
The odds were always against City after their - but they were offered brief hope of reaching the knockout phase as goals either side of the interval from David Silva and Yaya Toure put them in command against Bayern.
For a few tantalising moments City looked set to claim the precious qualifying place as Napoli struggled to break down Villarreal, but Etihad Stadium was plunged into eerie silence as news of the Italians' goals in Spain filtered through.
And on a black night for Manchester, City must now take their place alongside neighbours United - who also went out after losing 2-1 away to Basel - in the Europa League after learning harsh lessons of life in the Champions League during their first campaign.
Roberto Mancini's side have swept to the top of the Premier League, but even this expensive and richly talented side found the adjustment to Europe's elite competition a tough one, paying a heavy price for losses away to Bayern and the ultimately decisive defeat in Naples.
City will now make the Premier League an even bigger priority, while regrouping and planning again for what they hope will be another tilt at the Champions League next season.
Their ambition of qualifying from the group stage was helped by Bayern coach Jupp Heynckes' decision to relegate many of his key players to the bench, having already won the group. Goalkeeper Manuel Neuer, Philipp Lahm, Mario Gomez, Franck Ribery and Thomas Mueller all watched from the sidelines.
The change in personnel did not disrupt the discipline and organisation that is Bayern's trademark, however, as City were frustrated in all their attempts to exert early superiority.
City felt they were victims of an injustice after 16 minutes when Silva's free-kick floated straight in, but French official Stephane Lannoy adjudged that Joleon Lescott had fouled keeper Jorg Butt.
The breakthrough came six minutes before the interval, courtesy of another moment of instinctive skill from the magical Silva. Edin Dzeko's touch sat up nicely for the Spaniard and he made a difficult opportunity look easy by firing a wonderful left-foot volley into the bottom corner of Butt's goal.
City gained confidence from the strike and almost added a second immediately as Sergio Aguero cut through Bayern's defence only to see Jerome Boateng clear off the line.
Silva then forced another save from Butt with Gareth Barry shooting over from the rebound as City ended the half in the ascendancy.
And that supremacy was confirmed six minutes after the resumption with their second goal. Dzeko was again involved, slipping a neat pass through to the foraging Toure, who poked a right-foot finish past Butt.
City's fans were dreaming of achieving what had looked unlikely before kick-off and reaching the last 16, but the celebrations were snuffed out once Napoli took charge against Villarreal.
Having worked so hard to reach the Champions League, elimination will be a bitter blow for Mancini and City as they join neighbours United in Europe's second-string competition.