Manchester United crashed out of the Champions League on Tuesday with a 3-2 defeat at Wolfsburg, who made club history by reaching the knock-out stages.
German Cup holders Wolfsburg advanced to the last 16 for the first time as Group B winners thanks to their come-back win at the sold-out Volkswagen Arena.
The defeat puts United manager Louis van Gaal under pressure with his side now winless in their last four
PSV Eindhoven's 2-1 win at home to CSKA Moscow allowed the Dutch to claim second place at Manchester's expense as third-placed United now drop into the Europa League.
The Red Devils suffered a repeat of their 2011/12 European campaign when defeat in their final group game at FC Basel also denied them a place in the last 16.
Anthony Martial's early strike for the Red Devils was cancelled out by first-half goals from Brazil's Naldo and Portugal's Vieirinha for hosts Wolfsburg.
United drew level when Wolfsburg's French midfielder Josuha Guilavogui scored a late own goal seconds before Naldo claimed his second by heading the winner.
The result was an ideal tonic for Wolfsburg after suffering their first home defeat in 29 home games last Saturday when they lost 2-1 against Borussia Dortmund.
United arrived in Wolfsburg without injured striker Wayne Rooney and short on goals after scoring just once in drawing their three previous games.
But that problem was solved inside the opening ten minutes as the Red Devils took an early lead.
The game started at a blistering pace as Wolfsburg's Germany winger Andre Schuerrle cannoned his shot over the bar with only David de Gea to beat in the opening minutes.
United went ahead when Juan Mata thread a superb pass through the Wolfsburg defense for Martial to fire past Wolfsburg's Diego Benaglio on 10 minutes.
The hosts replied just four minutes later when left-back Ricardo Rodriguez, who injured himself in the process, fired in a free-kick which centre-back Naldo guided into the back of the United net.
Wolfsburg took the lead with a superb goal when Julian Draxler beat two United players and played a one-two with Max Kruse to offer Vieirinha a simple tap-in on 29 minutes.
Draxler should have made it 3-1 when he smacked his shot at De Gea moments later.
United looked to have equalized just before the break when Jesse Lingard curled home a cross from outside the area, but the linesman spotted Mata was offside and obscuring the vision of Benaglio.
The Red Devils got the goal they craved on 82 minutes when Marouane Fellaini headed down from a corner and Guilavogui steered the ball into his own net in an attempt to clear.
Manchester were level for just a matter of seconds though as Naldo was left unmarked from a corner and headed inside the near post on 84 minutes for the winning goal.
Only desperate defending from Wolfsburg in the dying stages kept United out as the Premier League side piled on the pressure, but to no avail.