Manchester City’s hopes of qualifying for the Champions League last 16 are looking grim after losing 3-1 at Ajax’s Amsterdam Arena in Group D.
Samir Nasri opened the scoring against the run of play in the first half but Ajax equalised just before the break through Siem de Jong.
City started the second period the better side but a Niklas Moisander header and deflected Christian Eriksen strike gave the Dutch champions a famous win.
City now prop up the group with one point, with Ajax on three.
Borussia Dortmund top it with seven points after beating Real Madrid, who have six points, on Wednesday.
Roberto Mancini gave Edin Dzeko a rare start after the Bosnian complained following his match-winning brace as a substitute against West Brom at the weekend.
Sergio Aguero looked the more dangerous player in a first half which City started poorly, largely watching as Ajax knocked the ball around with skill.
The Dutch champions lacked the outlet of a target man but caused problems. On nine minutes Christian Eriksen’s arrowing half-volley flew just wide after a chest-down and lay-off by fellow Dane Lasse Schone.
Captain Siem de Jong, operating behind Tobias Sana with former Liverpool winger Ryan Babel employed on the left side of attack, almost got a head on a cross in the 20th minute before Eriksen employed a subtle touch to beat James Milner then shot just wide from outside the area.
And on 22 minutes City took an undeserved lead. Micah Richards fed the ball over the halfway line and inside to Milner who picked out the run of Nasri into the box on the left and the France star finished into the far corner with aplomb.
That gave City impetus. Aguero was almost immediately denied a goal by a last-ditch block from Toby Alderweireld and the Argentina star again burst into the box two minutes later, with another great challenge denying him.