Manchester United were eliminated from the Champions League in controversial fashion as Cristiano Ronaldo returned to poke in Real Madrid's winner at Old Trafford.
Nani was erroneously red carded on 56 minutes by referee Cüneyt Çakır with United 1-0 ahead thanks to Sergio Ramos' own goal shortly after the interval.
Substitute Luka Modrić's rifled strike then levelled the match and the tie just after the hour mark before Ronaldo pounced three minutes later.
Nani was harshly red carded
The Portuguese's dismissal was another slice of luck for José Mourinho at Old Trafford, nine years after his Porto side were the benefactors of an egregious offside call against Paul Scholes after he scored legitimately. Mourinho offered Nani a sympathetic pat and appeared as baffled by the referee's decision as Sir Alex Ferguson was furious.
Madrid enjoyed the sterile domination but it was United who came closest to breaking the deadlock in an enterprising first half.
The ageless Ryan Giggs' corner was headed onto the post by captain Nemanja Vidić in the first 45's outstanding chance, while Diego López denied Robin van Persie and then the gamely Danny Welbeck with routine saves.
Gonzalo Higuaín meanwhile had a goal disallowed in front of the Stretford End when Madrid captain Sergio Ramos was penalised for a foul on Van Persie from a set-piece.
United broke the deadlock in untidy fashion after the pause when Raphaël Varane failed to clear and Nani's low cross was helped on by Welbeck to ricochet off the hopeless Ramos.
Muted celebration: Ronaldo came back to haunt United again
Nani, monitoring an aerial ball, then caught Alvaro Arbeloa accidentally to concede what appeared to be a foul and yellow card. Only Çakır decided otherwise and sent the perplexed Portuguese off to a cacophony of jeers.
Already struggling to retain possession with 11 men, United weathered the storm for 10 minutes before Modrić's fantastic strike swerved in off David de Gea's post. The selfless Higuaín then delivered an inviting cross for Ronaldo to capitalise at the far post to win the tie.
Veteran López denied Michael Carrick, Van Persie and Vidić as United delivered a spirited, yet fruitless, onslaught to the soundtrack of a defiant Old Trafford.
"The best team lost," shrugged a humble Mourinho. The last time he said that was when his Chelsea team were eliminated by Liverpool in 2005. It suited him more eight years ago.