Cristiano Ronaldo scored the goal that sent Manchester United crashing out of the Champions League against Real Madrid, although referee Cuneyt Cakir was the true Old Trafford villain after he sent Nani off as the Spaniards triumphed 2-1 on the night for a 3-2 aggregate scoreline.
United were extremely comfortable sitting on a 1-0 lead given to them by Sergio Ramos' 48th-minute own goal, but a red card for Nani - harshly given for dangerous play - changed the entire complexion of the contest.
Instantly Jose Mourinho sacrificed a defender for Luka Modric, who produced a breathtaking equaliser to square the tie. Then, almost inevitably, the largely ineffective Ronaldo had his moment as he slid home Gonzalo Higuain's cross to leave ten-man United needing two goals to rescue their European dream - a task that proved beyond them.
Sir Alex Ferguson took a major gamble prior to kick-off, leaving Wayne Rooney on the bench in an attempt to keep Xabi Alonso out of the game. His tactics worked supremely until the referee's intervention, and no amount of noise from the home crowd could prevent Madrid's comeback.
The visitors were quick to settle on foreign soil, Ronaldo seeing an early free-kick blocked by a red United wall before Higuain - preferred to Karim Benzema - curled wide when the ball broke kindly for him on the edge of the area.
United waited 14 minutes to threaten, but when they did it was the majesty of Ryan Giggs producing an outside-of-the-boot cross to Robin van Persie, who scuffed his volley on his favoured left foot.
Their next chance was even better. A corner from the right was headed against a post by Nemanja Vidic, and the rebound fell to Danny Welbeck four yards from goal. With keeper Diego Lopez already grounded next to the post Vidic had just hit, Welbeck - from an unnoticed offside position - somehow knocked the rebound directly at the keeper with the whole goal at his mercy.
Madrid's threat was sporadic, but they were denied a goal by a generous refereeing decision in favour of United midway through the first half, Ramos penalised for a foul on Van Persie when he won an aerial challenge. Higuain poked the resulting header home, but the whistle had already gone.
Within moments Van Persie was involved in another big chance for United at the other end, ramming a drive directly at Lopez, who spilled to Welbeck before making a miraculous recovery save.
United looked comfortable and the more likely team to score, so it was no surprise when they did three minutes after the break. Rafael's driving run eventually saw the ball find its way to Nani on the left side of the area, and his low cross was diverted in by Ramos after Welbeck had got a telling touch.
Then came the big moment. Nani, attempting to control a ball falling over his shoulder, caught Alvaro Arbeloa high to the chest with his studs. It appeared a foul without malicious nature, but the referee produced a red card to stun Old Trafford and bring a furious Ferguson to his feet.
Mourinho responded by throwing on Modric for Arbeloa, while Ferguson beckoned a wall of noise from the home fans. Instantly Madrid threw a catalogue of dangerous crossed across goal, but Rafael blocked Higuain's point-blank header on the goal-line.
Modric began pulling all strings for the Spanish side and he produced a wonderful equaliser, faking past Michael Carrick before rattling a 25-yard stunner in off David De Gea's post.
Then came Ronaldo's winner, touching home Higuain's cross before refusing to celebrate in front of United's desperately heartbroken fans. It was the winner they had feared from the man they still loved, although both Van Persie, Rooney and Vidic missed fine chances before the final whistle.
In the night's other tie, Borussia Dortmund easily disposed of Shakhtar Donetsk, winning 3-0 on the night for a 5-2 aggregate victory.
The German side came into the clash having claimed a hard-fought draw in Ukraine three weeks ago and Felipe Santana put them firmly on course for the next round with a thumping header just after the half hour.
Mario Gotze touched home Robert Lewandowski's cross shortly afterwards, while Jakub Blaszczykowski all but made sure of Dortmund's passage just before the hour.
The emphatic win underlined Manchester United boss Sir Alex Ferguson's comments that the Bundesliga team are one of the favourites for glory in this year's competition.