Newcastle United were knocked out of the UEFA Champions League and missed out on a place in the Europa League after they were beaten 2-1 by AC Milan.
It was a desperately disappointing night for Eddie Howe's side, who had they held on to their lead would have advanced to the knockout stages due to Paris Saint-Germain being held by Borussia Dortmund.
A draw would have given them third place in the group and a spot in the Europa League, but a 84th-minute winner from Samuel Chukwueze ended their stay in Europe altogether.
Meanwhile, Manchester City, who had already secured their place in the last 16 as Group G winners, edged a five-goal thriller against Crvena zvezda, also known as Red Star Belgrade, to maintain their 100 per cent record in this season's competition, with Micah Hamilton and Oscar Bobb scoring their first goals for the club.
How Newcastle's match unfolded
Knowing only a win would suffice, Newcastle started brightly and took the lead through Joelinton just after the half hour.
The Brazilian collected a pass just inside the area, before rifling a powerful effort into the top corner.
Milan pressed for an equaliser which came very much against the run of play on 59 minutes, when former Chelsea players Oliver Giroud and Christian Pulisic combined for the latter to tap in.
Galvanised by their goal, Milan began to turn up the pressure and Rafael Leao crashed his strike against a post.
And with six minutes remaining, Newcastle’s fate was sealed when substitute Chukwueze curled a superb finish high past Martin Dubravka.
Newcastle turn their attentions back to the Premier League when they host Fulham on Saturday.
Group F standings
| Team | Pts | Goal difference |
|---|---|---|
| Dortmund | 11 | +3 |
| PSG | 8 | +1 |
| AC Milan | 8 | -3 |
| Newcastle | 5 | -1 |
How Man City’s match unfolded
Pep Guardiola used this match as an opportunity to start a number of fringe and academy players, with 20-year-old Hamilton (below) scoring the opener 19 minutes into his Man City debut in Serbia.
Hamilton became the youngest English player to net on his Champions League debut since Marcus Rashford in 2017 for Manchester United (19 years, 316 days).
The defending champions would double their advantage on 62 minutes, when Bobb ended a jinking run with a curled finish for his maiden goal in a City shirt.
Hwang In-beom and Aleksandar Katai scored for Crvena either side of a Kalvin Phillips penalty as City became only the second English side after Liverpool in 2021/22, to progress with six wins from as many group matches.
Man City's next match is in the Premier League at home to Crystal Palace on Saturday.
Group G standings
| Team | Pts | Goal difference |
|---|---|---|
| Man City | 18 | +11 |
| RB Leipzig | 12 | +3 |
| Young Boys | 4 | -6 |
| Crvena | 1 | -8 |