Two dreadful decisions by the officials cost Spurs as they threw away a first-half lead to lose at the City of Manchester Stadium.
Darren Bent thought he had scored a late leveler against Sven Goran Eriksson's Manchester City side only for the assistant referee to wrongly flag for offside.
Earlier Stephen Ireland had equalised for the home side, tapping in from close range after Elano headed towards goal. Replays shows he was in an offside position.
Spurs had taken the lead in the first half, Pascal Chimbonda supplying Robbie Keane who beat Joe Hart with a sublime finish.
But City improved in the second half and were probably the better side after Ireland's controversial goal made it 1-1.
And Nedum Onuoha kept Man City's European hopes alive with a powerful header past Paul Robinson.
Spurs pushed forward for a late goal and Bent thought he had grabbed his side a point, only for a linesman to wrongly deny Spurs.
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