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Manchester United old boy Cristiano Ronaldo crowned his first match back at Old Trafford since leaving with the decisive goal that saw Real Madrid beat the hosts 2-1 in their Champions League Last 16 second leg clash and progess 3-2 on aggregate on Tuesday.
Victory - which an uncharacteristically humble Real manager Jose Mourinho said was undeserved - was gained against a United side reduced to 10 men with over half-an-hour to go when Nani was given a straight red card for a high tackle on Alvaro Arbeloa.
Defeat leaves the distinct likelihood of there not being a British club in the last eight for the first time since 1996 as both Arsenal and Celtic face overhauling 3-1 and 3-0 deficits respectively on trips to Bayern Munich and Juventus.
The night's other match was a much more clear-cut affair as German champions Borussia Dortmund eased to a 3-0 win over Ukrainian opponents Shakhtar Donetsk to book a last eight spot for the first time in 15 years when, as holders, they reached the semi-finals and were beaten by Real.
Real grabbed their two goals after going behind to a Sergio Ramos own goal and Nani's sending off as Luka Modric scored with a beautiful effort and then Ronaldo nipped in to add the second.
It all left Mourinho, who has already taken Porto and Inter Milan to Champions League glory, underwhelmed by his side's performance.
"The best team lost, independent of the sending off," Mourinho told ITV. "We didn't deserve to win and didn't play well."
United boss Alex Ferguson was replaced at the post-match press conference by his more temperate assistant Mike Phelan, who described the Scot as being "very distraught".
"It was a great performance marred by the wrong decision," added Phelan.
United had broken the deadlock early in the second-half as Nani's low cross was met by Danny Welbeck and his shot deflected off Real skipper Ramos and into the net.
However, Nani's contribution was to be brought to an abrupt and dramatic end when Turkish referee Cuneyt Cakir - who sent off Chelsea skipper John Terry in last season's semi-final against Barcelona - showed a straight red card at the Portuguese winger after he went in with his studs showing on Alvaro Arbeloa.
It prompted furious protests from the players and Ferguson, who shoved one member of his staff aside to descend the steps and remonstrate with the fourth official.
Mourinho removed Arbeloa almost instantly and sent on the attacking talent of Modric to try to force home the one-man advantage and it paid off within minutes.
The Croatian unleashed a superb curling effort from well outside the area that beat the diving David de Gea and three minutes later the whole game was turned around as Gonzalo Higuain slid a delightful low cross to the far post and Ronaldo was on hand to tap it into the net.
Dortmund, who had topped their first stage group, which also included Real, had taken an early grip on their match as Felipe Santana rose magnificently in the 31st minute and placed his header inside the top right hand corner.
Dortmund put it all but beyond Shakhtar's reach six minutes later as Robert Lewandowski picked out Mario Goetze who slotted home.
The hosts extinguished all hope in the 59th minute as Donetsk goalkeeper Andriy Pyatov spilled the ball and Polish international Jakub Blaszczykowski pounced to put it in the back of the net.
Dortmund's young coach Jurgen Klopp was ecstatic, though, he played down Ferguson's belief that his side could go all the way and emulate their win in 1997.
"There are still lots of strong teams in the competition," he said. "We are just delighted with the result and I am proud of the team.
"This is an exceptional performance, the whole Champions League campaign has gone like clockwork and this was an unbelievable 90 minutes from us.