Manchester United finished bottom of their Champions League group following a 1-0 defeat to Bayern Munich at Old Trafford.
Kingsley Coman's 70th-minute goal brought the late breakthrough after being played in by Harry Kane. Before that, there had been opportunities for United but Bruno Fernandes squandered the best of them on what was another disappointing night for Erik ten Hag.
With Copenhagen beating Galatasaray in the other game in Group A, United would not have been able to finish among the top two anyway. But defeat here, a fourth in six games in this competition, means Ten Hag's team are out of Europe altogether this season.
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How Man Utd exited Europe
Bayern had already secured top spot in Group A regardless of the result in Manchester but head coach Thomas Tuchel named a strong side as his team were determined to bounce back from their shock 5-1 away defeat to Eintracht Frankfurt on Saturday.
They stroked the ball around with trademark confidence in the early minutes. Kane and Joshua Kimmich had tame shots that did little to test Andre Onana. It was Luke Shaw with the more promising effort that Manuel Neuer could only divert over the bar.
Manchester United had been emphatically beaten 3-0 by Bournemouth at Old Trafford on Saturday but the recent victory over Chelsea offered hope that Ten Hag's team remained capable of raising their standards against ostensibly stronger opposition.
There were signs of that. United's pressing has been a strength this season and they were at their best when harrying high up the pitch, occasionally forcing Bayern into uncomfortable moments. The problems came when the German side played through them.
It should have brought the opening goal when Leroy Sane contrived to make a mess of a clear opening following Coman's cross. But United were well in it throughout the first half even if the loss of Harry Maguire to a groin injury disrupted them.
Shaw also departed at the interval, replaced by Aaron Wan-Bissaka. But with the scores level in Denmark as well as Manchester, United needed only to score a goal to leap from bottom of the table to second. And the chances came in the second half.
Fernandes really should have done better than blaze over the bar when free in the box after Wan-Bissaka's smart cut-back. Min-Jae Kim then had to produce a brilliant interception to prevent a tap-in for the onrushing United attackers. It was their moment.
But Copenhagen's opener against Galatasaray left United needing a goal in their favour at both grounds in order to qualify and as that news seeped down from the stands some of the energy levels seemed to dip too. It was no great shock when Bayern scored.
Kane was not at his very best on his return to English soil but his touch to put Coman through on goal was too good for the United defenders. The Frenchman fired past Onana and any lingering hope that Ten Hag's team could conjure something was gone.
The youngsters continued to chase the ball but it was a lost cause. Bayern extend their unbeaten run in Champions League group-stage games to 40 and can look forward to bigger challenges. When United will return to this competition remains to be seen.
Ten Hag: We had our moments
Ten Hag was pleased enough with the performance of his team even though the result went against him. "I think there was a good intensity in the game and from our side we brought Bayern out of their rhythm," he told reporters in the press conference afterwards.
"The defensive organisation we did quite well, if not very well, especially the first part of the second half where we had really good ball regains high up the pitch. Also, we had a very good chance from Bruno. So we had our moments but didn't take them."
That reflects the Champions League campaign as a whole, having led Copenhagen by two goals away from home and lost, and led Galatasaray by two goals away from home and drawn. Those are disappointments that Ten Hag will reflect on.
"We had the opportunities in games, in winning positions. We scored many goals so we have to see we gave it away sometimes by individual errors, not one player but more players, not every time the same, so we gave opponents opportunities.
"We had very good spells so we have to do better but the fact is: not enough points. We are disappointed. We should have done better."
Tuchel sympathises with Ten Hag
Almost always I feel sympathy for the other coach," said Tuchel.
"But we try everything to win matches, these are the goals of high-level sports. But, of course I have sympathy. He has a lot of key players injured for a decisive match, they lack the personality and maybe the width to change games from the bench.
"It is not an easy time but I am pretty sure he knows what to do next and he does not need my advice or clapping on the shoulders, he is experienced enough to go through it. I had not a nice moment last Saturday and sometimes you feel pretty lonely as a coach."
Asked if he was surprised to see United finish bottom, Tuchel added: "Yes, this is a huge club and not what you expect. In the group, you expect Manchester United also challenging to win the group and a place in the round of 16.
"But in my experience, I can tell you we had a difficult group. The matches were tight, the results were narrow so you could see everything was possible until today for Manchester United. In some of the matches, games changed in a blink of an eye.
"They were comfortable in the lead in Istanbul and gave it away, they were comfortable in the lead in Copenhagen. It is a big club. They are a dangerous team."
Man Utd's European exit in stats
- Manchester United have finished bottom of their Champions League group for just the second time, previously doing so in 2005/06.
- This is just the second time in the Champions League that Manchester United have lost two home group games in the competition, previously doing so in 1996/97 against Fenerbahce and Juventus.
- Manchester United have now lost 12 of their 24 games in all competitions this season, as many defeats as they suffered in the entirety of the 2022-23 campaign.
Maguire and Shaw limp off as Man Utd' injury crisis worsens
Maguire and Shaw limped off in Manchester United's Champions League tie with Bayern Munich, as Ten Hag's injury crisis worsens.
The double defensive blow means United have 13 players potentially unavailable ahead of this weekend's trip to Liverpool, live on Sky Sports.
- Marcus Rashford (illness)
- Anthony Martial (illness)
- Victor Lindelof (knock)
- Harry Maguire (groin)
- Luke Shaw (possible hamstring)
- Casemiro (thigh)
- Tyrell Malacia (knee)
- Lisandro Martinez (ankle)
- Christian Eriksen (Knee)
- Mason Mount (leg)
- Amad Diallo (knee)
- Bruno Fernandes (suspended)
- Jadon Sancho (disciplinary)
What's next?
Manchester United visit Liverpool live on Sky Sports this weekend on Super Sunday. Watch live on Sky Sports Premier League from 4pm, kick-off 4.30pm.
Bayern Munich return to Bundesliga action on Sunday, also live on Sky Sports on Sunday. Stuttgart visit the Allianz Arena live on Sky Sports Football from 6.20pm, kick-off 6.30pm.