By Phil McNultyChief football writer at Old Trafford
Manchester United's Champions League ambitions ended in controversial circumstances that left manager Sir Alex Ferguson and his players enraged at Old Trafford.
Sir Alex Ferguson is "distraught" after Real loss, says his assistant Mike Phelan
United looked on course for a place in the quarter-finals at Real Madrid's expense after Sergio Ramos's own goal just after half-time gave them a platform to build on the 1-1 draw from the first leg at the Bernabeu.
The tie was transformed by Turkish referee Cuneyt Cakir's decision to send off Nani for an aerial challenge on Real Madrid defender Alvaro Arbeloa after 56 minutes - a red card that reduced Ferguson and his players to fury.
Jose Mourinho's side, a subdued force until then, took advantage ruthlessly with two goals in three minutes from ex-Tottenham midfield man Luka Modric and former United golden boy Cristiano Ronaldo to move into the last eight.
Real wreck United's run
The defeat was Manchester United first in a Champions League knockout game at Old Trafford since February 2005 - a 1-0 defeat to AC Milan
Thanks to their win, Real Madrid are the only visiting team to have won more than once at Old Trafford in the Champions League
United responded superbly with a typical late rally that brought a series of fine saves from Real keeper Diego Lopez, but events midway through a dramatic second half settled the destiny of an enthralling game.
Ferguson's body language after Nani's dismissal screamed anger and injustice and he had good reason to feel United could well have been taking their place in the latter stages until the referee's intervention.
Mourinho now moves on towards his target of a third Champions League with three different clubs while United must concentrate on domestic matters as they close in on a 20th title with a commanding 12-point lead in the Premier League and a place in the quarter-finals of the FA Cup.
Ferguson's decision to drop Wayne Rooney was another of the bold selection decisions the Scot is adept at taking - he also gave Ryan Giggs his 1,000th professional appearance - and he was rewarded with a first half display that mixed strict defensive discipline with attacking threat on the break.
Ronaldo received a rapturous reception that echoed around Old Trafford, responding with a wave and a tap of the hand on his heart in return.
Real's superstar was kept at arm's length in the first half, wasting a free-kick then being frustrated by a fine challenge from United captain Nemanja Vidic when he finally found space in the area.
And Vidic came closest to breaking the deadlock in an engrossing contest when his header hit the post from a Giggs corner, with Danny Welbeck being ruled offside as he attempted to turn in the rebound.
Welbeck's energy and movement was a feature of United's play but he was unable to turn in an inviting rebound when Lopez failed to hold Robin van Persie's initial effort.
Ronaldo scores again
Cristiano Ronaldo has scored eight goals in eight Champions League games this season, and 18 in his last 18
Real suffered a blow towards the end of the first half when the dangerous Angel di Maria pulled up holding his hamstring and was replaced by Brazilian Kaka.
United did make the breakthrough three minutes after half-time when Nani won the ball back from Raphael Varane as he failed to clear in the area and his cross took the faintest touch off Welbeck before Ramos deflected the ball past Lopez.
It was reward for United's efforts - but events were to suddenly conspire against them and take this tie beyond their control after 56 minutes.
Nani went into a high challenge with Arbeloa but his eyes were on the ball throughout and United were stunned when referee Cakir waited for the Portuguese to get back on his feet before producing the red card.
Ferguson raced into his technical area to protest while United's players surrounded the official to no avail - United's manager then turning to all parts of Old Trafford and raising his arms and clenching his fists to plead for even louder support.
The best team lost - Real Madrid manager Jose Mourinho
It came but the sense that the game had taken a crucial turn against United was underscored as Real struck to make the most of their numerical advantage with two quick goals.
Mourinho's reaction to the red card was to replace Arbeloa with Modric, who took the opportunity to put his struggles at the Bernabeu behind him at the worst possible time for United with a fine equaliser after 66 minutes.
He showed a fine change of pace on the edge of the area before swerving a 20-yard shot past United keeper David de Gea and into the net via the post.
And, inevitably, Ronaldo made his impact with Real's second three minutes later, turning in Gonzalo Higuain's cross from a tight angle at the far post. His celebrations were muted but the travelling Real supporters packed into a corner of Old Trafford were ecstatic.
Rooney was introduced for Tom Cleverley as United showed the spirit and fight that is their trademark as they tackled an impossible task.
Lopez saved crucially from Michael Carrick and Van Persie while Rooney shot over and into the Stretford End from 10 yards.
The keeper also saved acrobatically from another Vidic header although Real remained dangerous on the break with Kaka hitting the post and Ronaldo bringing saves from De Gea.
A night of frustration was summed up by jeers aimed at the referee at the final whistle, jeers that soon turned to applause for United's disappointed players.
Full Time The final whistle goes and the game is over.
The ball is swung over by Cristiano Ronaldo, save made by David De Gea. Short corner worked by Luka Modric. Luka Modric decides to take the corner short. Luka Modric decides to take the corner short.
Corner taken by Robin van Persie from the right by-line, Nemanja Vidic takes a shot. Save by Rodriguez Diego Lopez.
Shot from 18 yards from Cristiano Ronaldo. Save made by David De Gea.
Effort from deep inside the box by Ricardo Kaka hits the post.
Booking Kleper Pepe shown a yellow card.
Substitution Rafael Da Silva goes off and Antonio Valencia comes on.
Cristiano Ronaldo takes a shot. Save by David De Gea.
The ball is swung over by Rafael Da Silva, Raphael Varane makes a clearance.
Robin van Persie takes a shot. Save made by Rodriguez Diego Lopez. Close range effort by Wayne Rooney clears the crossbar.
Corner taken short by Ashley Young. Michael Carrick takes a shot. Save made by Rodriguez Diego Lopez.
Luka Modric concedes a free kick for a foul on Patrice Evra. Free kick taken by Patrice Evra.
Shot from just outside the box by Michael Carrick goes over the crossbar.
Substitution (Man Utd) makes a substitution, with Ashley Young coming on for Danny Welbeck.
Luka Modric takes a shot. Save by David De Gea.
The assistant referee signals for offside against Cristiano Ronaldo. Rio Ferdinand takes the free kick.
Danny Welbeck takes a shot. Comfortable save by Rodriguez Diego Lopez.
Patrice Evra takes the free kick.
Substitution (Man Utd) makes a substitution, with Wayne Rooney coming on for Tom Cleverley.
Booking Booking for Ricardo Kaka for unsporting behaviour.
Ricardo Kaka challenges Rafael Da Silva unfairly and gives away a free kick.
Corner from left by-line taken by Ryan Giggs.
Booking Michael Carrick is cautioned by the ref for dissent.
Substitution Kleper Pepe replaces Mesut Ozil.
The assist for the goal came from Gonzalo Higuain. Ricardo Kaka gives away a free kick for an unfair challenge on Ryan Giggs. Ryan Giggs restarts play with the free kick.
68:18 Goal scored
Goal! - Cristiano Ronaldo - Man Utd 1 - 2 R Madrid Cristiano Ronaldo grabs a goal from close range to the bottom right corner of the goal. Man Utd 1 (2)-(3) 2 Real Madrid.
Garcia Sergio Ramos provided the assist for the goal.
65:52 Goal scored
Goal! - Luka Modric - Man Utd 1 - 1 R Madrid A goal is scored by Luka Modric from outside the area to the bottom right corner of the goal. Man Utd 1 (2)-(2) 1 Real Madrid.
Robin van Persie takes a shot. Save by Rodriguez Diego Lopez.
Centre by Luka Modric, clearance by Rio Ferdinand.
Inswinging corner taken right-footed by Luka Modric, Gonzalo Higuain takes a shot. Clearance made by Rafael Da Silva. Corner taken left-footed by Mesut Ozil. Xabi Alonso takes a shot. Save by David De Gea.
Corner taken by Mesut Ozil played to the near post, Nemanja Vidic makes a clearance.
Substitution Luka Modric comes on in place of Alvaro Arbeloa.
Effort on goal by Ricardo Kaka from just inside the area clears the bar.
Free kick crossed by Mesut Ozil, Robin van Persie manages to make a clearance.
Dismissal Luis Nani is shown a red card.
Free kick awarded for a foul by Luis Nani on Alvaro Arbeloa.
Robin van Persie challenges Garcia Sergio Ramos unfairly and gives away a free kick. Garcia Sergio Ramos takes the free kick.
Gonzalo Higuain crosses the ball.
Cristiano Ronaldo takes a shot. Blocked by Nemanja Vidic.
Outswinging corner taken left-footed by Mesut Ozil played to the near post, Robin van Persie makes a clearance.
Assist on the goal came from Luis Nani.
47:48 Goal scored
Goal! - Garcia Sergio Ramos - Man Utd 1 - 0 R Madrid Garcia Sergio Ramos concedes an own goal. Man Utd 1 (2)-(1) 0 Real Madrid.
The second half has started.
45:00 +1:01 Half time
Half Time The players leave the pitch at half time.
Cristiano Ronaldo has an effort at goal from outside the box which goes wide left of the goal.
Substitution Ricardo Kaka on for Angel Di Maria.
David De Gea takes the direct free kick.
Booking Alvaro Arbeloa receives a yellow card for unsporting behaviour.
Free kick awarded for an unfair challenge on Patrice Evra by Alvaro Arbeloa.
Robin van Persie takes a shot. Save by Rodriguez Diego Lopez. Danny Welbeck takes a shot. Save by Rodriguez Diego Lopez. Corner from the right by-line taken by Ryan Giggs, Header from close range by Nemanja Vidic misses to the right of the goal.
Alvaro Arbeloa gives away a free kick for an unfair challenge on Luis Nani. Patrice Evra takes the direct free kick.
Mesut Ozil takes the inswinging corner, Raphael Varane takes a shot. Save made by David De Gea. Gonzalo Higuain takes a shot. Save by David De Gea. Outswinging corner taken by Angel Di Maria from the left by-line. Garcia Sergio Ramos gives away a free kick for an unfair challenge on Robin van Persie. David De Gea restarts play with the free kick.
Gonzalo Higuain produces a cross, clearance by Michael Carrick.
Angel Di Maria crosses the ball, clearance made by Rafael Da Silva. Outswinging corner taken left-footed by Mesut Ozil from the left by-line to the near post. Mesut Ozil delivers the ball, Sami Khedira takes a shot. David De Gea makes a save.
Shot by Luis Nani. Garcia Sergio Ramos gets a block in.
Sami Khedira produces a cross, Cristiano Ronaldo takes a shot. Rafael Da Silva gets a block in.
Cristiano Ronaldo takes a shot. Nemanja Vidic gets a block in.
Tom Cleverley gives away a free kick for an unfair challenge on Alexandre Fabio Coentrao. Direct free kick taken by Alexandre Fabio Coentrao.
Danny Welbeck takes a shot. Blocked by Garcia Sergio Ramos. Corner from the left by-line taken by Luis Nani, Effort from inside the area by Robin van Persie misses to the right of the goal.
Sami Khedira challenges Patrice Evra unfairly and gives away a free kick. David De Gea takes the direct free kick.
Cristiano Ronaldo delivers the ball, clearance made by Tom Cleverley.
Corner taken by Ryan Giggs, Nemanja Vidic takes a shot. Save made by Rodriguez Diego Lopez. Robin van Persie is caught offside. Rodriguez Diego Lopez restarts play with the free kick.
Angel Di Maria takes the free kick.
Booking Patrice Evra receives a caution.
Free kick awarded for an unfair challenge on Angel Di Maria by Patrice Evra.
Luis Nani crosses the ball, Raphael Varane gets a block in. Luis Nani takes the inswinging corner, clearance made by Angel Di Maria.
Angel Di Maria fouled by Patrice Evra, the ref awards a free kick. Direct free kick taken by Angel Di Maria.
Free kick awarded for an unfair challenge on Michael Carrick by Mesut Ozil. Nemanja Vidic restarts play with the free kick.
The ball is sent over by Ryan Giggs, Robin van Persie takes a shot from 12 yards. Garcia Sergio Ramos gets a block in. Inswinging corner taken by Luis Nani from the left by-line. The referee blows for offside. Rodriguez Diego Lopez takes the direct free kick.
The ball is crossed by Luis Nani, clearance by Alexandre Fabio Coentrao. Robin van Persie takes a inswinging corner from the right by-line to the near post, Gonzalo Higuain makes a clearance.
Free kick awarded for an unfair challenge on Rafael Da Silva by Gonzalo Higuain. Ryan Giggs takes the direct free kick. Effort from the edge of the penalty box by Gonzalo Higuain goes wide of the right-hand upright.
Robin van Persie is ruled offside. Rodriguez Diego Lopez takes the free kick.
The ball is delivered by Angel Di Maria, Michael Carrick gets a block in. Corner from left by-line taken by Angel Di Maria. The ball is swung over by Xabi Alonso.
Free kick awarded for an unfair challenge on Xabi Alonso by Danny Welbeck. Xabi Alonso takes the free kick.
Robin van Persie is flagged offside by the assistant referee. Rodriguez Diego Lopez takes the direct free kick.
Garcia Sergio Ramos concedes a free kick for a foul on Robin van Persie. Ryan Giggs takes the direct free kick.
Alexandre Fabio Coentrao fouled by Ryan Giggs, the ref awards a free kick. Cristiano Ronaldo has an effort direct from the free kick.
Xabi Alonso is adjudged to have handled the ball. Rio Ferdinand takes the direct free kick.
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