Manchester United were dumped out of the Champions League after losing 3-2 to RB Leipzig on a disappointing night for Ole Gunnar Solskjaer.
United, who knew they only needed a point to qualify from Group H, fell 3-0 behind in Germany after a shambolic defensive showing with on-loan Manchester City full-back Angelino (2), Amadou Haidara (13) and Justin Kluivert (69) putting the hosts firmly in control.
However, a Bruno Fernandes penalty with 10 minutes remaining sparked United into life and Paul Pogba, subject of some controversial comments from his agent in the build-up, played a big part to get United back to 3-2 as his header deflected off Harry Maguire (82) and into the net.
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It left United with eight minutes to find an equaliser but despite a couple of hairy moments, Julian Nagelsmann's side held on to send Solskjaer's men into the Europa League.
The draw for the last-32 of the Europa League will take place from midday on Monday 14 December.
RB Leipzig: Gulacsi (7), Mukiele (7), Orban (7), Konate (7), Angelino (8), Haidara (7), Sabitzer (8), Kampl (7), Olmo (6), Nkunku (6), Forsberg (6)
Subs used: Poulsen (6), Kluivert (7), Adams (6)
Man Utd : De Gea (4), Lindelof (5), Maguire (6), Shaw (4), Wan-Bissaka (5), Matic (5), McTominay (6), Fernandes (6), Telles (4), Greenwood (6), Rashford (5)
Subs used: Pogba (7), Van De Beek (6), Williams (6), Tuanzebe (6), Fosu-Mensah (6)
Man of the match: Angelino
How it all unravelled for United...
United started with a back five as Luke Shaw was drafted in as the third centre-half and with Scott McTominay and Nemanja Matic protecting the defence, it was assumed United would be hard to break down in their bid for a point.
- Ole Gunnar Solskjaer made five changes to the United team that came from behind to beat West Ham at the weekend. David de Gea returned in goal, while Luke Shaw made his first appearance since last month’s 3-1 win at Everton. Bruno Fernandes, Marcus Rashford and Nemanja Matic were also recalled. Paul Pogba was named on the bench.
That was not the case as Leipzig found it easy to play through the lines and work their key players into space.
Angelino, allowed to leave on loan by Manchester City, got Nagelsmann's men off to a dream start by lashing home inside two minutes. Aaron Wan-Bissaka allowed him too much room while United's midfielders were too sloppy to allow the service into their roaming wing-back.
Haidara added a second soon after - and yet again it was completely preventable from a United point of view. Angelino clipped a ball in from the left and somehow United were outnumbered at the back post with Shaw and Alex Telles completely out of sync with their defensive responsibilities. Haidara took full advantage of the space, firing home past a helpless David de Gea.
United could easily have been 3-0 behind soon after as another diagonal ball to Angelino disrupted the visitors, only for unmarked Emil Forsberg to miss the target from close range.
The ball was in the net minutes later when Willi Orban turned home after Ibrahima Konate's header came back off the post. However, the video assistant referee ruled Orban had strayed offside and United had a reprieve.
A change of shape was employed after the break as Donny van de Beek came on for Telles as United reverted to a four-man defence. It triggered a response but they did not work Peter Gulacsi until 65 minutes on the clock as Fernandes struck a low drive from distance that needed clawing away.
The Portugual midfielder went even closer minutes later when seeing a dipping free-kick hit the bar from 20 yards as momentum was growing within the United ranks.
But, their bubble was burst a minute later and United were further behind.
Maguire allowed Christopher Nkunku to bobble a cross into the danger zone and Kluivert reacting quicker to clip the ball over De Gea, who did not cover himself in glory.
Going 3-0 down kicked United into fifth gear - and a potential comeback was sparked by Mason Greenwood winning a penalty after a Konate barge. Fernandes slotted home the spot-kick and United swiftly reduced the deficit further, with Pogba leaping highest to meet a corner at the far post and getting away a header that went in off Maguire and Konate.
McTominay and Marcus Rashford had efforts to level it up but the final act of the game was Gulacsi's preventing Nordi Mukiele from scoring an own goal as Leipzig progressed at United's expense.
'Ole got it horribly wrong'
Sky Sports' Paul Merson on Soccer Special:
"This is Manchester United. They need to be in the Champions League, not Thursday night football.
"That result tonight didn't show well for Solskjaer.
"If Leipzig had won 3-0 you would have come away and said 'Leipzig are the better team, they played better'. But when he changed it around, it came back to 3-2 and could have easily been 3-3. That just shows you that he got it horribly, horribly wrong at the start of the game.
"No disrespect to Southampton and West Ham, sometimes you can give them a goal head-start, but you cannot give these teams in Europe a two or three-goal head-start. You are going to get caught out and they got caught out in a big game. They would have been better losing to West Ham because there are plenty of games left in the Premier League. This has gone now.
"The biggest team in the world, in my opinion, are out of the Champions League."
Man of the match: Angelino
His influence on this match in the opening 20 minutes set the tone for Leipzig's victory. Wan-Bissaka decided to give him half a yard too many and he punished him with the sweetest of strikes to open the scoring. His aggressive style continued to push United back and it was his pin-point cross that led to the second goal. Angelino has now had a hand in six goals in six Champions League appearances this season (three goals, three assists). It's amazing to think Pep Guardiola allowed him to leave on loan, especially with Benjamin Mendy's inconsistent nature and Oleksandr Zinchenko not a natural in that position. On this showing, he's Manchester City's best attacking left full-back.
What the manager said
Manchester United boss Ole Gunnar Solskjaer: "You can't say we were good enough, we weren't.
"We started really well in this group and the big defeat was in Istanbul. That's the one you look back at and think that's where we lost the points we should have had.
"You cannot give a team a 3-0 lead and expect to come back. We were unlucky towards the end. I thought the effort and character was there.
"We knew we had to defend crosses, we knew we had to defend balls in the box and we couldn't clear them. As a footballer you can't feel sorry for yourself."
Opta stats - Ole's woe
- Man Utd have conceded 3+ goals in consecutive Champions League games for the first time since April 2003.
- Man Utd exited at the group stage in a Champions League campaign for the first time since 2015-16 under Louis van Gaal.
- Solskjær has lost six of his 10 UEFA Champions League matches as a manager (W4); the first manager to lose six or more times in their first 10 games in the competition while in charge of an English side.
- Since his Man Utd debut in February, no player in Europe's top five leagues has scored more penalties in all competitions than Bruno Fernandes (13 - level with Cristiano Ronaldo).
- Only against Juventus in April 1999 (11 minutes) had Man Utd been 0-2 down earlier in a Champions League match than they were today against RB Leipzig (13 mins).
Live Premier League
United have a derby day to look forward to on Saturday as Manchester City visit Old Trafford, live on Sky Sports.