Wolfsburg have recorded a 3-2 victory over Manchester United to ensure that the Premier League side exit the Champions League at the group stage.
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Two goals from Naldo and a routine finish from Vieirinha did the damage as United dropped into the Europa League due to PSV Eindhoven's 2-1 win at home to CSKA Moscow.
After an entertaining opening which saw Andre Schurrle squander an opportunity for Wolfsburg, United took the lead when Juan Mata put Anthony Martial in behind the defence before providing a cool finish past Diego Benaglio.
However, two minutes later, Wolfsburg were back on level terms when Naldo met a Ricardo Rodriguez free kick and volleyed the ball into the bottom corner.
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The early chances dried up but just before the half-hour mark, Marouane Fellaini nearly put United ahead for a second time, only to see his header well saved by Benaglio.
That intervention proved crucial as moments later, the home side went in front as a team move ended with Julian Draxler tapping the ball across goal for Vieirinha to provide the simple finish.
Wolfsburg threatened a third before half time, with Draxler seeing a shot from 12 yards kept out by David de Gea, though United thought they should have been level at the break after Jesse Lingard's cross went into the far corner, but Mata was adjudged to have distracted Benaglio from an offside position.
It took a while for the second half to burst into life, but on the hour mark, United showed their attacking intent inside the box and after Fellaini had managed to get the ball to Memphis Depay, the Dutchman produced a fine acrobatic effort that was punched clear by Benaglio.
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Four minutes later though, Van Gaal's men were indebted to the agility of De Gea, who, after advancing out of his goal, ran back to claw Schurrle's 35-yard effort past the post.
Max Kruse should have put the result beyond doubt just before the 70-minute mark, only to place a volley marginally wide, while at the other end, Depay curled a free kick just wide of the post.
With scenarios changing by the minute due to three late goals in the Netherlands, United found themselves needing two goals to make sure of qualification and they were halfway there when Josua Guilavogui put through his own net from a corner.
However, United's joy was short-lived as two minutes later, Wolfsburg regained the lead when Naldo powered a header past De Gea, despite the best efforts of a defender on the line.
United pushed forward in search of an unlikely comeback but Wolfsburg held firm to leave the English giants facing Europa League action after Christmas.
Darren Plant
