Three-time winner Manchester United crashed out of the Champions league on Tuesday, losing 3-2 to Wolfsburg which advanced to the round of 16 for the first time.
Anthony Martial put United ahead in the 10th before Naldo volleyed in the equalizer in the 14th. Vieirinha regained the lead for Wolfsburg in the 29th, before an own goal by Josuha Guilavogui in the 82nd tied the score.
But two minutes later Naldo scored his second with a header to seal Wolfsburg's victory and increase pressure on United coach louis van Gaal.
The loss, coupled with PSV Eindhoven's 2-1 home victory over CSKA Moscow, dropped United to third place in Group B, meaning that it will now play in the Europa league.
Wolfsburg won the group with 12 points and PSV also advanced with 10 points, two more than United.
United went ahead after a perfect through ball between two defenders from Juan Mata for Martial, who slotted past Diego Benaglio inside the far post, after Andre Schuerrle had wasted Wolfsburg's first chance in the third minute. Wolfsburg's reply came quickly when central defender Naldo volleyed home from a free kick from Ricardo Rodriguez, who limped off a couple of minutes later with a hamstring injury.
Benaglio produced a great reflex save on the line to deny Marouane Fellaini, who connected with a corner from Daley Blind.
Wolfsburg went ahead again after a spectacular move. Draxler wrong-footed Bastian Schweinsteiger and cut inside to swap passes with Max Kruse. Draxler then played the ball back to Vieirinha, who had the easy job of scoring from close range.
Goalkeeper David De Gea then saved United from an even bigger deficit. Schweinsteiger slipped and lost possession and Draxler brought United's defense into disarray before De Gea saved his shot.
United, which was missing captain Wayne Rooney, saw left back Matteo Darmian limp off with what looked a hamstring injury.
In the final minute of the first half, Jesse lingard found the net but the goal was disallowed because Juan Mata had lingered offside and hindered Benaglio.
Wolfsburg nearly scored in the 64th when De Gea ran far out of the box for no good reason and Schuerrle attempted a lob. But De Gea was on the run back and punched the ball away with one hand. He made another good save from Schuerrle before Kruse shot wide.
United earned a promising free kick at the edge of the penalty when Naldo pulled down Martial but Depay's shot curled outside the post. Naldo earned a yellow card that will keep him out of the next match.
The own goal came after Fellaini leaned on Dante and headed at the net. Guilavogui tried to clear but the ball ended in his own net.
United's glimmer of hope lasted only two minutes, before Naldo headed in from a corner, with Blind unable to block the ball on the line with his body.
lVG faces scrutiny after ucl exit
Manchester: louis van Gaal is 18 months and $375 million into his "process" of rebuilding Manchester United.
What's it got himIJ So far this season, a playing squad lacking balance and depth, accusations that he is betraying United's heritage of attacking football, and an ignominious exit from the group stage of the Champion league.
"United just look like an average team, and with an average team you are going to get average performances," former United great Paul Scholes said after a 3-2 loss at Wolfsburg on Tuesday consigned the team to Thursday nights in the oft-maligned Europa league.
Supporters of the increasingly embattled Van Gaal argue he has stabilized United after a period of upheaval following Alex Ferguson's departure in 2013 and David Moyes' ill-fated 10-month tenure. They'd say United is fourth in the Premier league, still has three trophies to play for this season and that it's too soon to make judgments, with transfer window looming.
Critics counter by saying it would be tough not to be in what appears to be the most open EPl title race in years — although Chelsea somehow has managed to be out of contention already. They'd say being in the Europa league is humiliating — former United defender Rio Ferdinand called it "embarrassing" — for a club of United's wealth and stature.