Manchester City were left facing a huge task to revive their Champions League campaign after crashing to a 3-1 defeat at Ajax.
Samir Nasri put them on course for victory in their vital Group D game in Amsterdam with an early strike but it came much against the run of play.
Ajax responded emphatically to get their first win of the competition - and leave City still looking for theirs - with goals from Siem de Jong, Niklas Moisander and, with the aid of a deflection, Christian Eriksen.
The defeat left the Barclays Premier League champions bottom of the group and staring at the possibility of failing to reach the knockout phase for a second successive season.
The hosts dominated possession for large spells although they were surprisingly unable to test goalkeeper Joe Hart enough.
City finally responded by breaking on 22 minutes and snatching the lead. Micah Richards raced clear down the right and fed inside to James Milner, who in turn set up Nasri for a clinical first-time finish over the diving Kenneth Vermeer.
Ajax began to assert themselves again as Ricardo van Rhijn found space and cut inside only to shoot over while Lasse Schone also missed the target and Ryan Babel fired straight at Hart.
The equaliser came on the stroke of half-time as Van Rhijn delivered a low cross along the edge of the area. Gareth Barry was unable to cut it out and De Jong met it with a fierce low strike which gave Hart no chance.
The Dutch side claimed the lead from a corner in the 57th minute as Moisander leapt in front of Joleon Lescott and glanced a header across Hart's goal into the bottom corner.
Babel had a route to goal blocked by Vincent Kompany but the hosts sustained the pressure and Eriksen ran across the area and shot past Hart with the aid of a big deflection off Gael Clichy.