Match ends, VfL Wolfsburg 3, Manchester United 2.
Manchester United were eliminated from the Champions League in dramatic fashion by a late loss at Wolfsburg.
The Red Devils made an ideal start when Anthony Martial caressed Juan Mata's pinpoint pass into the bottom corner.
Wolfsburg replied within three minutes through Naldo's sharp volley and led when Vieirinha finished a flowing move.
United thought they were through after Josuha Guilavogui's own goal, only to be condemned to the Europa League by Naldo's late header.
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Madchester's night of Euro madness
Louis van Gaal's side knew they would qualify for the last 16 by beating Wolfsburg, or if they matched PSV Eindhoven's result against CSKA Moscow.
Twice inside the final 15 minutes, United thought they were progressing at the expense of the Dutch side, who needed to better the Red Devils' result.
CSKA led 1-0 in Eindhoven as United trailed, before both PSV and United were briefly level in their respective games.
But late goals for Wolfsburg and PSV, who won 2-1, knocked out Van Gaal's team.
United's late misery was a stark contrast to Manchester City, who saw fortune swing back in their favour as their neighbours unravelled.
Five goals were netted inside six minutes across the two games, with City coming back to win 4-2 against Borussia Monchengladbach and pip Juventus to win Group D.
That means the Blues will avoid the likes of Barcelona and Real Madrid in the last 16, while the Red Devils face the prospect of Europa League football in the New Year.
Excitement, but an exit
Van Gaal has been criticised by some Red Devils supporters for his pragmatic, defence-minded approach - United were booed off after Saturday's 0-0 draw with West Ham at Old Trafford, the fifth time in nine matches they had failed to score.
However, United freed the shackles and produced an entertaining display in Germany, yet it was one that ultimately led to their exit from Europe's premier club competition.
Martial settled any early United nerves by racing on to Mata's perfectly weighted through ball, taking a touch before coolly sliding past Wolfsburg keeper Diego Benaglio.
Van Gaal's side continued to create chances, only to see Benaglio brilliantly stop Marouane Fellaini's first-half header and Memphis Depay's far-post volley after the break.
Fellaini's height caused problems at the corner which led to Wolfsburg midfielder Guilavogui flicking into his own net, but United were undone by their own defensive deficiencies.
Defensive horror show costs United
While United found a solution to their recent goalscoring woes, a suspect defensive display resulted in their downfall.
Wolfsburg threatened United with blistering counter-attacks and slick, one-touch passing around the penalty area.
But, more importantly, the Premier League side twice switched off at Wolfsburg set-pieces shortly after scoring themselves.
Injury-hit United had a makeshift defence, with young Uruguayan right-back Guillermo Varela making his first start for the club, and teenager Cameron Borthwick-Jackson playing for almost 50 minutes after replacing injured left-back Matteo Darmian.
It was a lack of organisation - and possibly experience - that allowed Brazilian defender Naldo to score the late winner.
Should Van Gaal have turned to experience?
Many observers were surprised Van Gaal decided to start 22-year-old Varela ahead of England international Ashley Young, while the exclusion of experienced holding midfielder Michael Carrick also raised questions.
Even more surprisingly, Young was still ignored when Darmian had to be replaced. Instead, Van Gaal turned to 18-year-old Borthwick-Jackson, who was making only his second United appearance.
England midfielder Carrick was eventually introduced for Germany's World Cup winner Bastian Schweinsteiger after 69 minutes, at the same time Mata was withdrawn for Nick Powell - the 21-year-old midfielder whose previous United appearance came in the 4-0 defeat by then-League One side MK Dons in August 2014.
Was disallowed United goal a turning point?
Van Gaal said afterwards that United were unfairly denied an equaliser shortly before half-time, a decision which he felt could have changed the complexion of the match and their Champions League future.
The visitors thought they had equalised when Jesse Lingard curled a 20-yard shot past Benaglio.
But their celebrations were cut short when the assistant referee raised his flag, after a long delay, for offside against Mata.
However, replays proved the official was correct with his decision. Despite not touching the ball, Mata's movement in front of Benaglio clearly impacted the Wolfsburg keeper.
Security alert holds up spectators
Spectators in the Volkswagen Arena were prevented from leaving the ground after a suspect package was found in a car park outside the stadium.
After approximately 15 minutes, fans were allowed to leave after police were satisfied it was not a bomb.
It did mean United's VIP flight back to Manchester, which included Van Gaal and his players, former boss Sir Alex Ferguson and former chief executive David Gill, was slightly delayed.
Stats you need to know
- United conceded as many goals in the first 30 minutes against Wolfsburg as they had in their previous nine games in all competitions
- Martial ended a run of 690 minutes without a goal in all competitions for United
- Wolfsburg beat United for the first time, having lost all three of the previous meetings
- Naldo scored in the Champions League for the first time since 2006
United legends react to exit
- 25NaldoBooked at 72mins
- 18Costa Santos
- 34RodríguezSubstituted forSchäferat 16'minutes
- 10DraxlerSubstituted forCaligiuriat 85'minutes
- 8Vieira de FreitasSubstituted forKloseat 78'minutes
- 17SchürrleBooked at 59mins
- 1de Gea
- 30VarelaBooked at 90mins
- 36DarmianBooked at 17minsSubstituted forBorthwick-Jacksonat 43'minutes
- 31SchweinsteigerSubstituted forCarrickat 69'minutes
- 8MataSubstituted forPowellat 69'minutes
- Milorad Mazic
- Shots on Target
Second Half ends, VfL Wolfsburg 3, Manchester United 2.
Corner, VfL Wolfsburg. Conceded by Jesse Lingard.
Guillermo Varela (Manchester United) is shown the yellow card for a bad foul.
Foul by Guillermo Varela (Manchester United).
Marcel Schäfer (VfL Wolfsburg) wins a free kick on the left wing.
Attempt missed. Nick Powell (Manchester United) right footed shot from outside the box misses to the right following a corner.
Attempt blocked. Jesse Lingard (Manchester United) right footed shot from the centre of the box is blocked.
Attempt blocked. Nick Powell (Manchester United) right footed shot from the centre of the box is blocked. Assisted by Michael Carrick.
Corner, Manchester United. Conceded by Maximilian Arnold.
Corner, Manchester United. Conceded by Marcel Schäfer.
Attempt blocked. Chris Smalling (Manchester United) left footed shot from the centre of the box is blocked. Assisted by Nick Powell.
Attempt missed. Memphis Depay (Manchester United) right footed shot from outside the box is high and wide to the right. Assisted by Marouane Fellaini.
Substitution, VfL Wolfsburg. Daniel Caligiuri replaces Julian Draxler.
Goal! VfL Wolfsburg 3, Manchester United 2. Naldo (VfL Wolfsburg) header from the centre of the box to the centre of the goal. Assisted by Marcel Schäfer with a cross following a corner.
Corner, VfL Wolfsburg. Conceded by Daley Blind.
Own Goal by Josuha Guilavogui, VfL Wolfsburg. VfL Wolfsburg 2, Manchester United 2.
Corner, Manchester United. Conceded by Diego Benaglio.
Offside, Manchester United. Michael Carrick tries a through ball, but Chris Smalling is caught offside.
Delay over. They are ready to continue.