Manchester United crashed out of the Champions League on Tuesday as they were beaten 3-2 by Group B winners Wolfsburg at the Volkswagen Arena on an evening of twists and turns.
United threw away an early lead and ultimately slipped from second to third in Germany as PSV moved into the top two behind Dieter Hecking's group winners - themselves battling back from Sergei Ignashevich's penalty to claim maximum points against CSKA Moscow.
Having endured another frustrating goalless draw against West Ham at the weekend, Anthony Martial gave United an ideal start when he slotted home the opener 10 minutes in.
However, things quickly turned as Naldo's volley levelled matters three minutes later before Vieirinha's first Champions League goal put Wolfsburg ahead at the break.
Missing captain Wayne Rooney, Louis van Gaal's men created chances but, as so often this season, failed to convert although Ignashevich's penalty briefly looked to have sent United through regardless.
Luuk de Jong levelled two minutes later for PSV before a Josuha Guilavogui own-goal looked to have given United a reprieve. The drama continued as Naldo restored Wolfsburg's lead before Davy Propper gave PSV the victory that condemned United to third place.
Van Gaal - having returned United to the Champions League after a season's absence - awaits Europa League football in 2016 as Wolfsburg celebrated their first group stage progression as winners.
Andre Schurrle was a surprise inclusion in Hecking's XI and he should have tested David De Gea two minutes in only to skew an effort over the crossbar when one-on-one.
With Rooney absent, Van Gaal handed Guillermo Varela a first United start and brought Memphis Depay into his starting line-up.
Marouane Fellaini was moved deeper into midfield to accommodate Depay and the Belgian found himself in the way of an early Juan Mata effort set for the target.
The Spaniard proved crucial in United's opener, however, playing in Martial who slotted the ball past Diego Benaglio.
Martial's first goal since October's draw with CSKA Moscow was soon cancelled out by Naldo's well-taken volley, the centre-back angling Ricardo Rodriguez's free-kick past De Gea.
Rodriguez was forced off injured soon after, replaced by Marcel Schafer, with Benaglio saving at close range from Fellaini before Wolfsburg took the lead with a delightful move.
Draxler cut in from the right and played a neat one-two with Max Kruse before setting up a tap-in for Vieirinha.
United's Matteo Darmian was also forced off injured - Cameron Borthwick-Jackson his replacement - with United's frustration boiling over when Jesse Lingard saw an effort chalked off for offside – the assistant referee deeming Mata was interfering with play when loitering in front of Benaglio.
United piled on the pressure but almost fell further behind to an audacious Schurrle lob amid questionable decision-making from De Gea with Kruse wasting an opportunity to put the game to bed when he sidefooted wide from a corner.
Drama in Eindhoven briefly threatened to alter the complexion of the group while Guilavogui's own-goal did the same. However, Naldo's second and Propper's winner in Eindhoven quickly dashed those hopes as Wolfsburg deservedly claimed the points and top spot and left Van Gaal with plenty to ponder.
‘After Manchester City’s recent form, maybe they’re the underdogs against Manchester United!’ Former Red Devils defender on this weekend’s derby
‘Arteta, Alonso, Emery, me… none of us were physical players – we needed the understanding of the game. That probably helped us move into management’: Premier League boss reveals reasons for natural career progression
