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Manchester City's heavy spending over the past few years in a bid for Champions League success look like ending in a first round exit for the second successive season after a 2-2 home draw with Ajax.
In contrast to City's woes modest Spanish side Malaga made light of it being their first appearance in the competition by qualifying for the knockout phase - after a 1-1 draw with AC Milan yesterday - and were joined by 2004 winners Porto, who drew 0-0 away at Dynamo Kiev.
City's hopes hang by a thread as with two matches to go they are five points adrift of second-placed Real Madrid, who had to twice come from behind to draw 2-2 at home to Borussia Dortmund, who top the group on eight points.
Ajax are third on four points and City manager Roberto Mancini believes his side are all but out.
"We conceded two stupid goals. In a very important game like tonight, you can't concede two goals from corners. Now we can do nothing, it's finished."
City, having taken just one point from their opening three fixtures - including a shock loss in Amsterdam – looked out for the count after an atrocious start.
Their defence was all at sea as Siem De Yong netted a double in the opening 19 minutes.
But an acrobatic effort from Yaya Toure put the English champions back in the contest and then Sergio Aguero fired home a leveller midway through the second period.
However, no late winner was to be forthcoming, although substitute Mario Balotelli was denied a late penalty claim after having his shirt tugged in the area.
"We did enough to win the game but we have to learn from this - we probably let ourselves down (on the goals)," said City captain Vincent Kompany.