roberto mancini's men were unable to conjure the win needed to keep their qualification hopes alive as ten-man madrid sealed their own progress.
real madrid cf advanced to the last 16 of the uefa champions league once again after a draw at manchester city fc which confirmed the english title holders' early elimination for the second year running.
karim benzema's early goal put madrid in control but city fought back to earn a draw through sergio agüero's spot kick after 74 minutes when álvaro arbeloa was shown red for the visitors. that goal kept city unbeaten at home in 20 european ties, a small consolation on the night their fate was sealed. roberto mancini's men remain bottom of group d, a point behind afc ajax in the pursuit of a uefa europa league place, while madrid's failure to win confirmed they will finish second behind borussia dortmund.
for city, madrid's goal summed up the defensive shortcomings that have cost them dear. mancini had lamented their lapses in concentration in his programme notes and the same happened again as maicon allowed benzema to ghost in behind the home defence and volley in angel di maría's cross from close range.
city were starting with a back three of pablo zabaleta, vincent kompany and matija nastasić, supported out wide by maicon and aleksandar kolarov, but the premier league's meanest defence was opened up with ease during the opening half-hour.
back on mancunian turf for the first time since leaving old trafford, cristiano ronaldo showed some typically smart footwork as he twice engineered crossing opportunities but sami khedira, the beneficiary both times, was off target. ronaldo then broke through and lifted his shot over hart yet nastasić cleared superbly off the line and the portuguese failed to convert on the rebound. another near miss followed as khedira broke through but was foiled by hart.
"we'll fight to the end," sang the city fans as their already faint hopes dimmed further though agüero provided a glimmer with a dipping shot that ıker casillas tipped over. then maicon stormed into the box after a one-two with agüero but steered his shot wide.
at half-time mancini switched to a back four with kolarov making way and javi garcía stepping into midfield against his old club. the game was tighter now and on the hour carlos tévez entered the fray as mancini went for broke.
moments later agüero looked certain to volley in maicon's cross at the far post yet somehow casillas got his body in the way. agüero made amends with the equalising goal, tucking away the penalty after going down in the box under a challenge by arbeloa. madrid lost the full-back to a red card but josé mourinho's men were the ones with something to celebrate at the finish.
