Bayern Munich needed a stoppage-time goal to see off Celtic and secure a place in the last 16 of the Champions League on Tuesday, while AC Milan were dumped out by Feyenoord and both Club Brugge and Benfica also advanced. In Germany, Bayern were defending a 2-1 lead over Celtic in their play-off tie from last week’s first leg but the Bundesliga leaders were unable to put the tie to bed, with Harry Kane hitting the bar before half-time.

Instead it was Celtic who went ahead on the night on 63 minutes thanks to Nicolas Kuehn, the former Bayern player, who slotted low into the net after a failed attempt to win the ball by Kim Min-jae.

That meant the tie was heading for extra time, but Bayern ultimately would not need to go that far as they scored in the fourth minute of injury time.

Alphonso Davies bundled the ball in from close range to make the score 1-1 on the night and clinch the tie for six-time European champions Bayern 3-2 on aggregate.

Vincent Kompany‘s team will find out their last-16 opponents when the draw is made on Friday, but it will be either German rivals Bayer Leverkusen or Atletico Madrid.

“Of course, we always want to dominate and be much better than the opponent, especially here. But the result is always the most important thing,” Kompany told UEFA.com

It was a heartbreaking way for Celtic to go out but the Scottish champions will take heart from their performance over the two legs.

“It never looked like we were going to concede the goal that we did and sadly for us, we did. I can only take immense pride from the performance and the guys gave everything,” said Celtic manager Brendan Rodgers.

Earlier, seven-time European Cup winners Milan were eliminated by Feyenoord, a 1-1 draw at San Siro taking the Dutch club through 2-1 on aggregate.

Santiago Gimenez, playing against the club he left just last month, had put Milan ahead on the night from close range in the first minute to level the tie on aggregate.

However, Milan had Theo Hernandez sent off early in the second half for a second booking, and Feyenoord levelled on the night through Julian Carranza on 73 minutes.

The visitors had Givairo Read shown a red card at the end of the game after they had held on to win the tie.

They could now come back to San Siro in the next round, with Inter Milan and Arsenal their two possible opponents.

Benfica and Club Brugge through

In Lisbon, Benfica drew 3-3 at home with Monaco to win their play-off tie 4-3 on aggregate and go through to play either Barcelona or Liverpool next.

Having won 1-0 in Monaco last week, the Portuguese giants extended their aggregate lead when Kerem Akturkoglu opened the scoring on the night midway through the first half.

Monaco came roaring back with Takumi Minamino and Eliesse Ben Seghir netting either side of half-time to level the tie on aggregate.

Vangelis Pavlidis scored a penalty, his seventh goal in his last six Champions League games, to make it 2-2 on the night, only for substitute George Ilenikhena to hit back for Monaco.

However, the tie swung decisively back towards Benfica as Orkun Kokcu made it 3-3 on the night on 84 minutes.

“It was a tough night, we knew Monaco would put pressure on us from the start and we felt it, we didn’t play our best game,” Kokcu told broadcaster SportTV.

“Still, we’re happy to have progressed to the last 16. I’m happy to have contributed to the result.”

Teenage starlet Chemsdine Talbi scored twice as Club Brugge claimed a 3-1 victory away to Atalanta in Italy to win their tie 5-2 on aggregate.

Talbi’s brace was followed by a superb Ferran Jutgla strike as the Belgians built on their 2-1 win at home in last week’s first leg and advanced to a last 16 tie against either Lille or Aston Villa.

Atalanta had 29 attempts on goal but were punished on the break by the Belgians and Ademola Lookman’s reply at the start of the second half was scant consolation.

Lookman also had a penalty saved while Atalanta captain Rafael Toloi was sent off late on, as last season’s Europa League winners bowed out.

The remaining play-off second legs will take place on Wednesday, with the standout fixture seeing Real Madrid defend a 3-2 first-leg lead at home to Manchester City.

Gustaf Nilsson shot Club Brugge to a 2-1 win over Atalanta on Wednesday with a controversial penalty in stoppage time to boost the Belgians’ chances of reaching the last 16 of the Champions League. Atalanta looked to be escaping Bruges with a draw after Mario Pasalic’s fine header four minutes before half-time levelled Ferran Jutgla’s fabulous opener for the hosts. But Nilsson won and then netted the decisive penalty at the Jan Breydel Stadium, delighting home fans and enraging Atalanta who could barely believe that the spot-kick had even been awarded.

Atalanta coach Gian Piero Gasperini stormed down the tunnel before the final whistle in anger while his players continued to protest at the end of the match, collecting only a series of bookings from unrepentant referee Umut Meler.

Nilsson had crumpled to the turf after being grazed on the face by Isak Hien’s left fingers as the Atalanta defender ran to collect the ball in his own area.

Hien couldn’t believe his eyes when Meler pointed to the spot and gave Nilsson the chance to fire Club Brugge to a win which they might have otherwise deserved for their enterprising performance in front of passionate home support.

“All I could see is that he (Meler) was arrogant, if you tried to speak to him he just handed out yellow, yellow, yellow,” said Charles De Ketelaere whose return to his home town and boyhood club was marred by the late penalty drama.

“I’ve only just seen the footage and I reckon that if you ask 100 people if that was a penalty all 100 would say no. It’s very strange.

“It hurts to lose right at the end like that. And it’s definitely not right.”

Club Brugge take a slender lead to next Tuesday’s second leg in Bergamo where Atalanta will be fired up to go through and face one of Aston Villa or Lille in the next round.

Penalty anger ‘pointless’

But the Serie A team will have some work to do get through, as they battle injuries, including key attacker Ademola Lookman, and were clearly rattled by their opponents at various points in the match.

“It’s pointless to talk about the penalty, I think anyone who watches football knows that was never a penalty,” said Marten de Roon.

“But what we need to do is look at our performance today which was not good… we need to be better if we want to get through.”

Club Brugge tore into the sluggish away side from the first whistle, doing to Atalanta what Atalanta usually do to other teams with intense pressure and high energy in chasing down the ball.

Atalanta were off the pace and it was an uncharacteristic mistake from Hien which led to Jutgla’s opener, with Chemsdine Talbi pouncing on a sloppy pass before setting up his Spanish teammate for a fine finish.

But moments before the break Pasalic struck the leveller in the only short period of the match in which Atalanta were on top.

Brugge again came out all guns blazing after the break but although Gasperini was left baffled by Atalanta’s performance it was his team that created the two best chances of the game around the hour mark.

First Simon Mignolet did brilliantly to keep out Davide Zappacosta’s close-range header and then substitute Lazar Samardzic blasted well wide a great chance to put Atalanta in the lead with the goal at his mercy.

That appeared to be it until Nilsson hit the deck and Meler gave Club Brugge a penalty which could be decisive in the tie.

Manchester City have reached do-or-die territory in the Champions League earlier than expected ahead of what Pep Guardiola has described as a “final” against Club Brugge on Wednesday. City have disproved the suggestion a new format to Europe’s top club competition would remove any jeopardy for the top clubs as Guardiola stares down the barrel of failing to make the Champions League knockout stages for the first time in his career. The English champions have endured a torrid season both in their Premier League title defence and on the continent.

A run of one win in 13 games, which included Champions League defeats to Sporting Lisbon and Juventus, between October and December was the nadir of City’s fall from grace.

Guardiola’s men have since turned a corner in the Premier League, winning four of their last five games to climb back into the top four.

But the deeper problems at the heart of City’s struggles were exposed last week as Paris Saint-Germain roared back from 2-0 down to inflict a damaging 4-2 defeat on the 2023 champions.

The loss of Ballon d’Or winner Rodri to a season-ending knee injury in September has been a devastating blow and compounded by a series of fitness issues at centre-back, where Ruben Dias, Nathan Ake and John Stones have all missed large chunks of the campaign.

Former captain Kyle Walker shocked the club with a request to leave earlier this month before joining AC Milan on loan.

All of which has forced City to rip up their initial plans and spend big in the January transfer window.

More than 120 million pounds ($150 million) has already been splashed on Egypt forward Omar Marmoush and young defenders Vitor Reis and Abdukodir Khusanov.

However, that trio will not be able to help against Belgian champions Brugge, who have not lost in 21 games in all competitions, as they are not eligible for this stage of the Champions League.

“We would not be doing it if our players were fit but today I think we have two central defenders, no more than that, and with our holding midfielders we are struggling,” said Guardiola of the January splurge.

“After eight years together we have so many players who are more than thirty years old and the other reason is the amount of problems we have with players’ availability. It is an absolutely normal process.”

Guardiola eyes ‘bigger success’

City sit 25th in the 36-team table and must finish in the top 24 to avoid elimination.

But victory will guarantee progress as Brugge sit three points above them with an inferior goal difference.

Despite their issues, some of Europe’s top clubs will be watching events closely at the Etihad Stadium hoping City do not scrape through only to hit their stride in the knockout phase.

Bookmakers still have them as sixth favourites for the competition behind Liverpool, Real Madrid, Arsenal, Barcelona and Bayern Munich.

Ake and Dias could be back for the playoff round next month, while Marmoush, who scored 20 goals for Eintracht Frankfurt this season, would be free to play in the next round.

Guardiola is confident his side will eventually rekindle their former glories.

“There are seasons where there are a lot of difficulties. It’s (about) how you stand up to it,” he said.

“When Rodri is here, when the defenders are here, when many players are here, we will not be 25th in the Champions League.

“Sometimes when you experience these situations and then you achieve it is a bigger success.”

But after winning just two of their opening seven Champions League games, they have no margin for error left if they are to avoid an embarrassing early exit.