Manchester City are out of the Champions League at the group stage for the second successive season after they were held to a draw by Real Madrid at the Etihad.
Roberto Mancini's side needed victory to maintain any hope of progress but fell behind to Karim Benzema's early goal.
Real threatened to run riot in the early stages as former Manchester United star Cristiano Ronaldo - given a predictably hostile reception - saw an effort scrambled off the line and Sami Khedira wasted three opportunities.
Mancini's three-man defensive system was being easily exploited by Real but City finally came into the game when the necessary alterations were made after the break.
Sergio Aguero equalised from the spot after 74 minutes following a foul by Alvaro Arbeloa, who was sent off after receiving a second yellow card, but even a late rally could not bring the goal they needed.
City are rooted to the bottom of Group D without a win and only three points from five games so the Premier League champions can have no complaints about making yet another early exit from the Champions League.
Mancini's own record in the competition, both with City and Inter Milan, also remains a disappointment and harsh lessons will have to be learned if a third venture into the tournament is to bring better results.
Jose Mourinho's La Liga champions were not wholly convincing and he marched off at the final whistle without the traditional handshake with counterpart Mancini, who had moved towards the edge of the pitch to console his players.
City's task was arduous enough without conceding yet another of the cheap goals that have scarred this disappointing European campaign.
Real were ahead inside 10 minutes when Angel Di Maria crossed from the right, leaving Benzema to apply the easiest of finishes as veteran defender Maicon switched off, leaving Mancini shaking his head in disgust in the technical area.
City were in danger of being torn apart as Real swept forward to put City's back three under
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