Manchester United bowed out of the UEFA Champions League and European competition this season with a 1-0 home defeat to Bayern Munich on a night of bitter disappointment compounded by injuries to defensive duo Harry Maguire and Luke Shaw.
Arsenal, who had already secured their passage from Group B with victories in four of their first five matches, were held to a 1-1 draw by PSV Eindhoven but still finished top of the table.
How Man Utd's match unfolded
Man Utd's task was clear - they needed to beat Bayern and hope Copenhagen and Galatasaray drew when they met in Denmark.
Erik ten Hag was unable to call on forwards Anthony Martial and Marcus Rashford, who both missed training on Monday due to illness, while Bayern were at full strength, with Harry Kane partnering former Manchester City striker Leroy Sane up front.
Kane, making his first club appearance in England since leaving Tottenham Hotspur for Germany in the summer, drew a smart save from goalkeeper Andre Onana after 10 minutes.
Joshua Kimmich had another effort saved by Onana, while Raphael Varane, making his first start since 24 October, used all his experience to make a couple of solid defensive blocks for Man Utd.
The Old Trafford faithful, keeping constant tabs on what was going on in Copenhagen, roared their approval when left-back Shaw let fly with a stinging effort that goalkeeper Manuel Neuer pushed behind for a corner.
Sane had a great chance to put Bayern 1-0 up after 32 minutes, but he was unable to get a clean connection at the back post from Kingsley Coman's pass.
United were forced into two defensive changes, first Maguire was replaced by Jonny Evans shortly before half-time and then Aaron Wan-Bissaka came on for Shaw at the start of the second period.
At the halfway stage, results elsewhere were falling in Man Utd's favour - they just needed a goal to send them through.
Bruno Fernandes fired over from Wan-Bissaka's pass before Scott McTominay and Antony were unable to get a touch on Alejandro Garnacho's dangerous cross as United started the second half with intent.
But as news filtered through that Copenhagen had taken the lead against Galatasaray, their hopes of progressing started to fade.
The Red Devils dream of reaching the round of 16 suffered a hammer blow with 20 minutes remaining when Kane's flick played in Coman, who picked his spot emphatically.
It was the 15th goal they had conceded in the Champions League this season, the most by an English side in the group stages of the competition, and there was to be no way back for United who finished bottom of the group.
Group A standings
| Team | Pts | GD |
|---|---|---|
| Bayern | 16 | +6 |
| FC Copenhagen | 8 | 0 |
| Galatasaray | 5 | -3 |
| Man Utd | 4 | -3 |
Man Utd return to Premier League action on Sunday when they face old foes Liverpool at Anfield.
Victory for Ten Hag's side, who were thrashed 7-0 in the corresponding fixture last season, would place United level on points with fifth-placed Spurs.
How Arsenal's match unfolded
Arsenal were already sure of a place in the last 16 as Group B winners and Gunners boss Mikel Arteta used the opportunity to rotate his squad, making eight changes from the team beaten at Aston Villa.
Arteta also named Academy prospects Karl Hein, Ethan Nwaneri, Lino Sousa and Reuell Walters as substitutes.
PSV, like Arsenal, were already assured of second place in the group, and they caused a few early problems for the Gunners.
A combination of Gabriel and goalkeeper Aaron Ramsdale made crucial blocks to deny Ricardo Pepi from close range on seven minutes and Yorbe Vertseen's 20th-minute header hit the woodwork.
Mohamed Elneny nearly marked his first start since January with a goal as the Gunners started to create chances of their own, but the midfielder's drive crashed against the foot of the post after 30 minutes.
Arsenal were far from their fluent best in the opening half, yet they went ahead three minutes before half-time with a fine piece of control and low finish from Eddie Nketiah.
PSV were back on level terms only six minutes after the break with a perfectly placed strike by Vertessen that went in off the inside of the post.
Arteta responded by making a trio of changes on 63 minutes with Declan Rice playing the remainder of the match at centre-back, while Elneny went off moments after receiving treatment on what appeared to be his hamstring.
Both teams then traded scoring chances in quick succession - Reiss Nelson smashed into the side netting before Ismael Saibari hit the post for PSV.
The only time Arsenal had previously won five of their group matches in a single season was in 2005/06, when they went on to reach the final.
And Arteta's side came agonisingly close to equalling that achievement in the dying seconds when Nketiah's close-range shot was superbly saved by Walter Benitez before substitute Leandro Trossard fired the follow-up over.
Group B standings
| Team | Pts | GD |
|---|---|---|
| Arsenal | 13 | +12 |
| PSV | 9 | -2 |
| Lens | 8 | -5 |
| Sevilla | 2 | -5 |
Arsenal will look to get back to winning ways on Sunday when they return to Premier League action at home to Brighton & Hove Albion.
Wednesday's matches
In the Champions League St James' Park will be bouncing as Newcastle United host AC Milan in a must-win match at 20:00 GMT, while Manchester City visit Crvena zvezda, also known as Red Star Belgrade, at 17:45 GMT.
Newcastle must beat Milan and hope that Borussia Dortmund can deny Paris Saint-Germain a victory to book their spot in the last 16.
Pep Guardiola's Man City have already confirmed their place in the knockout phase.