Manchester City went down fighting as their Champions League hopes ended with a battling 1-1 draw against 10-man Real Madrid at the Etihad Stadium.
Manager Roberto Mancini was again left to rue a costly decision to deploy a three-man defence as the Spanish giants tore into the hosts in the early stages. Karim Benzema struck and Real should have had more in a devastating spell.
But City grew in confidence after switching formations and Sergio Aguero levelled from the spot after Alvaro Arbeloa was sent off. City poured forward in search of a winner in the closing stages but it was not to be and the result leaves them with just three points in Group D and unable to progress.
Mancini had fielded Edin Dzeko up front in place of Carlos Tevez but any illusion of City solidity was soon shattered. Fabio Coentrao first got behind the City defence after seven minutes but Vincent Kompany managed to cut out his cross. Benzema then broke clear but Aleksandar Kolarov managed to get back to prevent him cutting inside and shooting.
City failed to heed either of those warnings and were soon punished as Maicon was left well out of position and Benzema peeled away from him to turn in a curling deep cross from Angel di Maria at close range. Cristiano Ronaldo thought he had doubled the lead himself when he deftly lobbed Joe Hart but Matija Nastasic chased back to hook off the line.
City finally made their presence in the game known after 21 minutes as Aguero turned to shoot after combining with David Silva but Iker Casillas palmed over. City earned a free-kick just after the half-hour when Arbeloa pulled back Aguero but Kolarov curled his shot wide.
City started the second half strongly with Maicon twice getting forward to deliver dangerous crosses. With Javi Garcia on in place of Kolarov, Yaya Toure also got forward to support the attacks more. Silva again weaved his way through the defence to tee up Aguero but Casillas denied the striker.
Mancini sent Tevez on but Aguero continued to look the main threat and he seemed certain to score as he reached Maicon's deflected cross, but Casillas produced a brilliant point-blank save. City were almost caught out again by Ronaldo, whose dipping shot troubled Hart but City cleared before he got a second attempt.
The hosts dragged themselves back level when referee Gianluca Rocchi pointed to the spot after Dzeko played in Aguero from a long Toure ball. Aguero went down after tangling with Arbeloa and what seemed a harsh decision was compounded for Real as the former Liverpool man was shown the red card.
Aguero coolly converted to level the scores. City pushed for a winner with Dzeko getting into a good position and Tevez shooting at Casillas. Coentrao also made a good interception to prevent a Maicon cross reaching Dzeko. Toure shot well over in injury time as City's night ended in disappointment and Real's place in the last 16 was confirmed.