Manchester City staged another late recovery but were eliminated from the Champions League after a 1-1 draw against 10-man Real Madrid.
A late Sergio Aguero penalty gave the scoreline some respectability for Roberto Mancini's team but a sober evening showed how far they have to go to compete on the highest club stage with a team of Real's calibre.
Jose Mourinho's side took an early grip of Wednesday's match through a 10th-minute Karim Benzema volley and they never looked like relinquishing until City threw caution to the wind late on.
Alvaro Arbeloa was sent off after conceding a soft penalty when he clipped Aguero with 17 minutes left and the Argentine stepped up to level the scores.
But it was not enough to stop City exiting the competition with one match to play, as Real joined Group D leaders Borussia Dortmund in the knockout stages.
Real Madrid dominated the opening 20 minutes at Etihad Stadium as they carved open City's leaky defence at will.
But the visitors only had Benzema's early goal to show for their initial excellence.
In what has been a familiar theme this season, City played Angel Di Maria onside, the Argentine swung in a ball that found Benzema in oceans of space on the edge of the six-yard box and the Frenchman gleefully belted in the opener.
Cristiano Ronaldo went close doubling Real’s advantage five minutes later but Matija Nastasic made an invaluable contribution by clearing off the line.
Mancini threw caution to the wind after the break, sending on Carlos Tevez after an hour to join Aguero and Edin Dzeko in attack.
After 73 minutes, Aguero burst into the box and was clipped from behind by Arbeloa, who received his second yellow card, and the forward stepped up to coolly finish from the spot.
It proved to be too little and too late, as City were once again left to reflect on their shortcomings in Europe.
In Amsterdam, Borussia Dortmund recorded a 4-1 win over Ajax in the other Group D fixture.
The visitors needed only eight minutes to open the scoring via Marco Reus, before Mario Goetze doubled their lead with a fine finish.
A somewhat fortunate Robert Lewandowski strike then put the match to bed shortly before the interval, and the Polish striker made it four after the break.
Substitute Danny Hoesen pegged one back for the hosts in the closing stages.