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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 pressure, with midfield man Khedira twice unable to provide the end product to Ronaldo's fine approach work.
Ronaldo also had a shot scrambled off the line and City keeper Joe Hart had to race out at the feet of Khedira as Real looked to put the game out of reach in an impressive opening phase.
City, however, offered moments of hope. Aguero was a threat and had a shot pushed over by Iker Casillas while Maicon suggested he would be of more service in an attacking sense rather than defensively with a positive run that ended with a finish poked just wide.
Mancini made a switch at half-time, sending on Javi Garcia for Aleksandar Kolarov. He also reverted to a more orthodox back four. It prompted a far more positive approach after the break and he further added to City's attacking resources by sending on Carlos Tevez for Samir Nasri on the hour.
It took a remarkable block from Casillas to deny City an equaliser when Aguero stole in on Maicon's deflected cross. A goal looked certain but the goalkeeper clawed the Argentine's effort away.
City's increased endeavour was rewarded with an equaliser and red card for Arbeloa with 16 minutes left. Aguero went down as the pair tangled and once the former Liverpool defender had been sent off the Argentine easily scored from the spot.
As the game entered five minutes of stoppage time, which was greeted with sarcastic applause by Mourinho, Tevez was inches away from getting on the end of another astute pass from the outstanding David Silva.