Jude Bellingham has not travelled to Germany for Real Madrid’s Champions League round-of-16 first-leg clash against RB Leipzig due to an ankle injury.

The England midfielder was not named in the Real squad for the trip after a sprained ankle forced him off in Saturday’s 4-0 win over surprise LaLiga title rivals Girona – but not before he had scored a brace.

Bellingham has scored 20 goals in 31 appearances for Real and rapidly become one of their most important players but manager Carlo Ancelotti is confident his side can cope.

“We have to think that Bellingham isn’t here, but we’ve won four out of four games without him,” the Italian said at his pre-match press conference. “Those who have replaced him have done very well, like Brahim (Diaz) or Joselu.

“He’s a very important player, but I think this has been an opportunity to get more motivated.

“We arrive on the back of a good run – the form is good. We are up against a good side with plenty of quality that plays a high-tempo game.

“We have shown lots of character, and credit to the team. The vibe is good.”

Leipzig boss Marco Rose, who coached Bellingham at Borussia Dortmund in 2021-22, is not convinced the 20-year-old will not feature on Tuesday.

Speaking at his pre-match press conference on Monday, he said: “I won’t believe that Jude will be out until he’s not in the stadium tomorrow.

“I know Jude, I know that he will do everything to play a Champions League game.”

Even without Bellingham, Ancelotti has plenty of star-power to choose from, but Rose insists his side will not be intimidated.

“We’re certainly not afraid,” he said. “We’re looking forward to the opponent, to the task, to our stadium. That’s what we want. What we worked hard for last season and now in the group stage.

“Real Madrid have developed outstandingly this season and become one of the strongest teams in Europe. They are in exceptionally good shape – in all areas.

“They know what it means to play in the Champions League and win it too. And we know about their qualities.

“But we’re not that bad and we have great footballers in our ranks. We will give everything and look for our opportunities to develop a good starting position.”

Defender Mohamed Simakan is in contention despite picking up a knock in the weekend Bundesliga draw at Augsburg, while midfielder Amadou Haidara has stepped up training after picking up a knee problem on Mali duty at the Africa Cup of Nations but remains doubtful.

Pep Guardiola has told Erling Haaland to focus more on getting his body language right than scoring goals.

The Manchester City manager admitted to being concerned about the prolific Norwegian’s demeanour since his return to action following a two-month lay-off with a foot injury.

Guardiola feels the striker has been preoccupied with adding to his remarkable goal tally and wants him to relax more.

He thinks Saturday’s victory over Everton was a good example, when Haaland had a quiet first half before netting twice late on to secure a 2-0 success.

Guardiola, speaking in Denmark at a press conference to preview Tuesday’s Champions League last-16 clash with FC Copenhagen, said: “Erling is young, playing in the most difficult position on the pitch surrounded by four or five players with minor space.

“In the first half maybe we didn’t have the special delivery players, like Kevin (De Bruyne) for example, who can find him.

“In that moment he has to be positive. When he scored a goal, he reacted but he doesn’t need to score because he helps us for many things.

“He is defined on goals but it is not just scoring a goal. As much it’s how he is clapping, encouraging his mates and the first intense press. This is what we need from Erling.

“But we cannot forget he has been two months out, which is a lot of time for a guy who is so tall.

“Back to the dynamic is not easy. He’s a huge competitor who wants to score goals. OK, we know that, so relax.

“If we don’t score today, or if he doesn’t score in 10 minutes, it’s OK. In the process he has to try because the team always wins when they overcome bad moments.”

Guardiola did stress this was a minor problem and he has no doubts about the 23-year-old.

“It looks like I am complaining about Erling but it was in general,” the City boss said. “How many games did Erling play and how many goals? His body language is not a problem.

“If he doesn’t score tomorrow, the day after or next week, it’s not a big issue.

“He’s so strong. It comes from nature. He’s coped perfectly because he’s so strong mentally. He scores one goal and wants a second and a third.

“You see his numbers at his age. In the Champions League not even (Lionel) Messi or Cristiano (Ronaldo) had these numbers at his age.”

City are hoping to silence a raucous atmosphere at Parken to take the initiative after the first leg of their tie against Copenhagen.

The Danes have not played competitively for two months due to their winter break but Guardiola expects a stern challenge from a side that finished above Manchester United and Galatasaray in their group.

He said: “I would say they are starving to compete and hungry and have full energy, fresh in legs and mind.

“I don’t know the rhythm but they have had lots of time to prepare for the game. Hopefully we can be in a good level to compete.

“It’s back to business in the competition but huge respect for the opponents. It was not an easy group and they did really well in all the games.”

Jurgen Klopp will leave Liverpool at the end of the 2023-24 season.

In an emotional announcement, released via Liverpool's media channels on Friday, Klopp confirmed this campaign would be his last at the helm at Anfield.

Klopp, who is under contract at Liverpool until 2026, claimed he is running out of energy, and after nearly nine years in charge, he will be leaving the club as a legend.

While Liverpool will hope to round off the German's time in charge with a second Premier League title, and possibly further trophies – they are already in the EFL Cup final – the Reds will also have to face the daunting prospect of what comes next.

Regardless, Klopp is set to leave as one of the club's most successful managers. 

With the help of Opta data, we break down Klopp's time in charge.

An Anfield giant

Bill Shankly, Bob Paisley, Kenny Dalglish. Klopp will take pride and place among the list of great managers to have taken charge of one of England's most successful clubs.

Since replacing Brendan Rodgers in October 2015, Klopp has taken charge of 466 matches, winning 283 of those. His win percentage of 60.7 makes him the best Liverpool manager in that metric, at least as far back as Opta's records go.

Klopp has lost just 78 games, while drawing 105. His team have scored 972 goals, an average of 2.1 per match.

Not that it has always been easy. In his first season – 2015-16 – his win rate was 44.2 per cent. However, it has never dropped below 50 per cent in a single campaign since then, with the low mark coming last term (50 per cent).

Klopp is the only Liverpool manager to win each of the top-flight, European Cup/Champions League, FA Cup, and League Cup with the club, while he has five major honours as it stands, which ranks him behind only Dalglish, Paisley (both six) and the great Shankly (13).

His Liverpool side peaked between 2018 and 2020. After reaching the Champions League final in 2017-18, the Reds won their sixth European Cup the following season, before then breaking their Premier League duck in 2019-20, albeit they wrapped up that title behind closed doors. They had also won the Super Cup and Club World Cup earlier that term.

The FA Cup and EFL Cup were both won in 2022 en route to what could have been a historic quadruple.

Liverpool still have four trophies left to play for this season. They sit top of the Premier League as it stands; they will face Chelsea in the EFL Cup final; they are into the knockout stage of the Europa League and they have a home tie against Norwich City in the fourth round of the FA Cup coming up on Sunday.

Klopp's best season based purely on win percentage came in 2021-22, when Liverpool won a remarkable 73 per cent of their games in all competitions, only to fall short of pipping Manchester City to the title on the last day of the Premier League season, before losing to Real Madrid in the Champions League final.

A European master

Klopp started as he meant to go on when it came to European football with Liverpool, leading the Reds to the Europa League final in his first season in charge.

Though they lost to Sevilla on that occasion back in 2016, Liverpool have gone from strength to strength in continental competitions. They were undone by Gareth Bale's magic and Loris Karius' error in Kyiv in 2018, but left all in Europe in their wake when they overcame Tottenham in Madrid a year later, having signed Alisson to ensure they had a top-class goalkeeper between the posts.

Liverpool were back in the showpiece match three years later. Again, it was Madrid they faced, and again Los Blancos came out on top – Vinicius Junior's goal and Thibaut Courtois' heroics enough to deny Klopp his second Champions League crown.

Klopp will not manage Liverpool again in the Champions League, meaning his 61.5 win percentage (40/65) in the competition will be maintained. His Liverpool team have scored an incredible 144 Champions League goals - an average of 2.2 per game.

Unbeaten runs, Guardiola rivalry and dominating the derby

The rivalry between Klopp's Liverpool and Pep Guardiola's Man City has been the lifeblood of the Premier League over recent seasons. 

While Liverpool are not exactly cash-strapped, they do not have the state-backed wealth that City enjoy, yet Klopp has managed to keep the Reds highly competitive – on two occasions, they have finished just one point below City with points tallies that in almost any other circumstance would have surely seen them win the title.

Since Klopp's first Premier League game, Liverpool have taken 671 points, a tally that trails only City (716), while the Reds have a positive goal difference of 367 (675 goals for, 308 goals against).

As it stands, Klopp is the Premier League's third-most successful manager based on points per game, with his 2.12 ranking behind only Alex Ferguson (2.16) and Guardiola (2.34).

His next victory in the top flight will bring up his 200th as Liverpool manager, from what will be his 318th such match in charge.

Only Guardiola (18 with City between August and December 2017) has been on a winning run as long as Klopp has in the Premier League, with Liverpool having rallied off 18 straight wins between October 2019 and February 2020. The Reds had previously gone on a 17-game winning streak between March 2019 and October 2019, a run that was ended by a 1-1 draw with Manchester United. 

Liverpool went on a 44-game unbeaten streak, meanwhile, between January 2019 and February 2020. Arsene Wenger (49 games between May 2003 and October 2004) is the only Premier League manager to have gone more successive matches without defeat.

Klopp has gone up against Guardiola on 24 occasions, making City the team Liverpool have faced the most in his time at the club. He has claimed 10 wins (41.7 per cent), lost six times and drawn eight games.

Of the four other 'big six' clubs, Chelsea rank as Klopp's least favourite, with just a 27.3 per cent win record from 22 matches (six victories). Klopp has faced Manchester United, meanwhile, on 18 occasions, winning seven times (36.8 per cent).

Meanwhile, Klopp has dominant form in the Merseyside derby. From 18 such meetings, Liverpool have lost just once to Everton, with that defeat coming at Anfield, behind closed doors, in 2021. The Reds have beaten the Toffees 11 times under Klopp (61.1 per cent).

Of the current Premier League sides, Klopp has claimed 12 victories over Bournemouth from 15 meetings, with that win percentage (80) his best against any side he has faced over six times.

Superstar Salah, fearsome front threes and flying full-backs

The story goes that Klopp was not initially in favour of signing Mohamed Salah from Roma back in 2017, but his arm was twisted by Liverpool's then-recruitment guru, Michael Edwards. If that is indeed true, then Klopp will no doubt be thrilled he was swayed to bring in the Egyptian.

Salah has scored 204 goals in 332 appearances for Liverpool, 84 goals more than any other player under Klopp (Sadio Mane – 120 goals from 269 appearances).

Only Roberto Firmino (355) has played more times for the Reds in Klopp's tenure than Salah, whose 306 starts puts him out in front. The 31-year-old has totalled up 27,037 minutes, over 2,000 more than next-best Firmino (24,903).

Salah also tops the charts for goal contributions (286), having added 82 assists on top of his strike tally.

Firmino and Mane, Salah's partners in crime in what was arguably the most feared forward line in world football, chipped in with 182 and 157 goal contributions respectively.

Meanwhile, Klopp has given more debuts to teenagers than any manager in Liverpool's history (42). One of those teenagers was Trent Alexander-Arnold, who along with Andrew Robertson, became pivotal to Klopp's heavy metal football.

The flying full-backs have been assist machines: Alexander-Arnold has created 78 goals in 298 appearances, while Robertson has crafted 63 from 275 games.

Just Firmino and Salah have played more minutes under Klopp than Alexander-Arnold (24,323) and Robertson (23,498). 

What's next?

Whoever replaces Klopp has big shoes to fill, and this might well end up being Salah's last season at Anfield too, as Saudi Pro League clubs circle.

Xabi Alonso and Julian Nagelsmann have been some early names touted around, but until the end of May, it will be all about the Kop bidding goodbye to Klopp.

He deserves a hero's farewell.

The European Super League's pledge to stream all matches for free is unsustainable and merely a ploy to coax fans into supporting the project.

That is the view of finance expert Dan Plumley, who does not see how a breakaway competition could offer enough prize money to earn the support of clubs while showing games for free. 

Despite a backlash from fans, players and media thwarting the Super League's attempted launch in 2021, the project reared its head again this week with a reworked format being announced.

After the European Court of Justice (ECJ) ruled FIFA and UEFA "abused a dominant position" in blocking the Super League two years ago, the competition's organisers, A22 Sports, revealed a new format for the tournament, which is still supported by Real Madrid and Barcelona. 

The plan features promotion and relegation across three tiers and also includes a promise to make all games free to stream, but Plumley doubts whether that is possible.

"Everything we've seen throughout history would point to the fact that won't be sustainable, which is where the finances and the distribution models get interesting," he told Stats Perform. 

"We've seen the proposed format of the new ESL but we've not seen the financial distribution mechanisms, we've not seen where the money's coming from and if you are going to promote a free-to-air model through a streaming service, that obviously looks good for the fans.

"But at some point you have to have some form of broadcaster to be able to generate prize money and to generate the finances of the competition. 

"Everything I've seen throughout the years would suggest that you can't go that long without a decent broadcasting deal or big commercial and sponsorship partnerships." 

Asked whether the promise of free coverage was purely intended to get fans onside, Plumley added: "Yeah, for sure. 

"You've probably made the most relevant point there, which is how much people are paying currently for sports subscription content. 

"Talking from a basis of us being located in the UK, it's not cheap. If you want a Sky Sports subscription, a TNT Sports subscription, the Amazon one… it does become quite costly for the fans. 

"So to have something that is free at the point of consumption is obviously a hook for fans to come on board with it. 

"I think we've clearly seen the backlash in the UK with the English clubs and many English fans. 

"Even if it is free-to-air and dependent on the clubs that would be involved, I think some would still turn around and say: 'No, thank you very much. Even if it's free, I'm not interested'. 

"But there is a whole range of international fans out there that follow European football and follow some of these clubs. Maybe some of those are interested. 

"You look at it through your own lens, but you also have to look at it through the lens of others. Obviously it's a ploy to try and get some positivity on board by offering it free-to-air."

Plumley said the only way the project could succeed financially with a free-to-air model was through the potential involvement of a state wealth fund.

"I think where you might see some shift in the future, and this might start to make it bigger than Europe, is will we see sovereign state wealth funds or private equity consortiums get involved with the financing of the competition, to enable them to show some free-to-air content?" Plumley said.

"In the 2021 project, it was supposed to be financed by JP Morgan and we saw that American influence, we've seen an explosion in Saudi Arabian football in the last couple of years. 

"Do one of those other big players in the market get involved in the future? I think all those questions are a little bit up in the air at the minute. 

"At some point, you have to start talking about broadcasting deals because there's only so much free-to-air content you can give away if you're going to be putting a load of prize money on the table."

Holders Manchester City will face FC Copenhagen in the last 16 of the Champions League.

Arsenal, the current Premier League leaders, will take on Portuguese side Porto in the first knockout round.

The ties, the first legs of which will take place over two weeks in February 2024, were confirmed after the draw at the Swiss headquarters of organiser UEFA in Nyon on Monday.

City played Copenhagen – who came through a group that included Manchester United – in the early stages last season, winning 5-0 at the Etihad Stadium and drawing 0-0 in Denmark.

Pep Guardiola’s side, who are currently in Saudi Arabia for the Club World Cup, qualified this time with a 100 per cent record in Group G.

Arsenal were also convincing winners of Group B on their return to the competition after a six-season absence.

Their opponents Porto came through as runners-up to Barcelona in Group H.

Spanish champions Barca, meanwhile, were handed a tough task against Serie A winners Napoli.

In the other ties, record 14-time winners Real Madrid were paired with RB Leipzig and their city rivals Atletico drawn against Inter Milan.

Paris St Germain will play the fourth Spanish side in the draw, Real Sociedad, with the two German teams, Bayern Munich and Borussia Dortmund, tackling Lazio and PSV respectively.

As winners of their groups, City and Arsenal will play the first legs of their ties away.

The first legs will take place on February 13, 14, 20 or 21 with the return matches on March 5, 6, 12 or 13.

Eddie Howe has challenged his Newcastle players to book themselves another crack at the Champions League after seeing them slip out of Europe in dramatic fashion.

At one point on Wednesday evening, the Magpies were heading for the last 16 of European football’s premier club competition, but they ended it empty-handed after AC Milan came from behind to snatch a 2-1 win at St James’ Park.

That booked them a Europa League berth and ended Newcastle’s continental involvement for the season, but a disappointed Howe is targeting a swift return.

He said: “I’d love the opportunity to do that again and I think that has to be our focus very quickly. I don’t think we can look at anything other than that.

“We want to be there again and we’re still close enough in the Premier League to do that and compete. All these things happen for a reason, I’m a believer in that.

“The ambition is there, of course. It’s there from all of us – but doesn’t mean it’ll happen. We have to make that happen.

“Any time you don’t achieve what you want, you have a setback, you have a disappointment, you have to use it as fuel and that’s very much has always been my way.

“The pain that you feel now is motivation for tomorrow. We now have to focus on the Premier League and have to try to make sure we get our form in the Premier League as strong as we can.”

The defeat by Milan – the Magpies’ third on the trot in all competitions – came courtesy of goals from Christian Pulisic and substitute Samuel Chukwueze after Joelinton had blasted them ahead.

They will resume domestic action against Fulham on Saturday sitting in seventh place in the table, seven points adrift of Manchester City in fourth.

While their domestic home for has been excellent, Newcastle have won only once on the road and with their injury problems starting to abate – Callum Wilson, Sean Longstaff and Dan Burn were all involved against the Italians – Howe is calling for a fresh focus.

He said: “I don’t want a hangover from this. We have to learn from it and quickly put it away.

“The players need to believe how good they can be, how good we are and this is a good test of that for us because of what’s happened in the last week.

“Football is an amazing thing, isn’t it? You go back 10 days and we had just beaten Manchester United with our best performance of the season. Then three games later, we’ve had three defeats.

“That’s football.”

Newcastle boss Eddie Howe defended his players after a Europa League place slipped from their grasp as they tried to secure a Champions League berth.

The Magpies were dumped out of Europe all together as a result of their 2-1 home defeat by AC Milan on a night when they had one foot in the last 16 of the premier competition, then looked destined for the lesser only to end up empty-handed.

Had the game finished 1-1, Howe’s men would have taken the group’s Europa League spot with Paris St Germain having secured second place behind group winners Borussia Dortmund after a 1-1 draw in Germany, but substitute Samuel Chukwueze’s late strike ensured it was the Serie A side who claimed it instead.

Asked if they might have played for a draw as time ran down, Howe said: “We wanted to qualify for the Champions League for sure. That was very much our intention before the game and in-game.

“I’m not sure in that moment you can take that will away from the players. If you look at the goals we’ve conceded, they’ve come from mistakes that can happen in any moment whether you are being proactive or reactive.

“Of course I take ownership of that, but I’d much rather have the intention to go and attack and to try to win rather than the other way round.”

Joelinton’s 33rd-minute piledriver had put Newcastle in the driving seat and their position improved further when Dortmund went ahead, but PSG levelled minutes later and crucially, so did the Italians through Christian Pulisic.

Goalkeeper Mike Maignan managed to turn a goal-bound Bruno Guimaraes shot on to his crossbar as the Premier League side sought the victory which would have kept them in the competition, but Chukwueze’s late intervention amid a chaotic conclusion proved decisive.

Howe said: “We’re desperately disappointed. It’s tough to take at the moment. The lads played very well in that first half and I thought we were good value.

“I was hoping the goal would come earlier than it did. Second half, we wanted to try to consolidate that and look for the second goal.

“I was really disappointed with the first goal we conceded because I think that is the key moment. We didn’t deal with a second-phase set-play well enough – it was an uncharacteristic goal, really, for us to concede and then the game became very transitional.

“It was end-to-end from both teams, both teams looking to win, and we conceded on one of those transitions.”

For opposite number Stefano Pioli, who headed into the game at St James’ Park under pressure and with former striker Zlatan Ibrahimovic having been drafted in as a senior adviser, there were mixed feelings.

Pioli said: “We definitely wanted to continue our path in the Champions League and that is very difficult. It was a bittersweet evening.

“What we could do this evening we did. Of course we’re disappointed about the Champions League and we regret it. Clearly we’re disappointed, but we also have the conviction that we’re a team that can do well.”

Celtic manager Brendan Rodgers was delighted to see his players break through a Champions League barrier with a last-gasp 2-1 victory over Feyenoord at Parkhead.

Substitute Gustaf Lagerbielke headed home in stoppage time to seal Celtic’s first victory in 16 Champions League group games, stretching back to Rodgers’ first spell in charge, and their first at home for a decade.

Celtic were consigned to bottom spot in Group E after matchday five but the win ensured they improved on last year’s total to finish on four points.

“It was a big moment because it’s been so long. Since I was here the first time it’s all that’s been talked about, a win in the Champions League at home. They have now cleared that barrier and we can look forward now.

“I said to the players, it wasn’t a burden they had to carry, especially a lot of the new players, but clearly the longer it goes on…

“It shows the challenge of the Champions League. But we are very determined over the course of my time here to improve on that record.

“I have been really pleased with some of the performance levels, especially at home, we have shown we can play at a high level and compete but of course you have to get results.

“To get the win draws a line under that home record and we can hopefully qualify next season and go into it fresh and the players can gain confidence knowing they can win at this level.”

Celtic had conceded in the 82nd minute and looked set for further late anguish after Luis Palma’s 33rd-minute penalty put the home side in front.

“The players showed they learned throughout the process we have been in this year because we have seen games over the years where the equaliser comes and the other team go on and get the winner,” Rodgers said.

“You have to tip your hat to the players because the mentality was very good. Some people may have thought this was a nothing game but this meant everything to us in the process we are in, to get the victory and to feel the confidence.”

Sweden defender Lagerbielke came off the bench for Stephen Welsh for his first appearance since September 30 and his first in the Champions League since being sent off in Rotterdam in the opening game.

Rodgers said: “It was a great moment for him because he hasn’t been involved in squads, other guys have been in front of him. But his attitude in training in the main has been superb and he has always been ready.

“The irony of him being sent off and then getting the goal was great, a really nice moment for him.”

Feyenoord head coach Arne Slot had claimed ahead of the game that he felt sorry for Celtic because they had – like his team – had no luck whatsoever during their Group E campaign.

After the game, Slot said: “You have to credit Celtic for the way they played in their whole Champions League, maybe apart from when they had 10 men against Atletico Madrid.

“So I think they deserved, from their point of view, a little bit of luck. They came away with one point from their previous two home games despite outplaying both opponents.

“So they deserved a little bit of luck and we are the team that gives teams a little bit of luck. You don’t have to thank me for that, but that’s what we do.”

Newcastle were knocked out of the Champions League after AC Milan came from a goal down to win 2-1 at St James’ Park.

Newcastle started the brighter of the two sides and made their first-half pressure count when Joelinton rifled a superb strike past Mike Maignan and into the top corner to give them the lead at the break.

Milan shifted into the gear in the second period and found an equaliser through Christian Pulisic, but the decisive moment came with six minutes to go when Samuel Chukwueze curled home from inside the area to earn their spot in the Europa League.

Paris St Germain secured their place in the last 16 of the competition with a 1-1 draw at Borussia Dortmund.

The French side’s Champions League hopes were thrown into doubt when Dortmund took the lead early in the second half as Karim Adeyemi swept home from close range.

But they were not ahead for long as Warren Zaire-Emery found the bottom corner, which proved vital to send PSG through from Group F in second place.

In Group G, Manchester City made it six wins from six games with a 3-2 away victory over Red Star Belgrade.

Debutant Micah Hamilton powered into the roof of the net to give Pep Guardiola’s side the lead and they looked on their way to a comfortable victory when Oscar Bobb rolled home, but Belgrade responded through Hwang In-beom.

City re-established their two-goal lead thanks to Kalvin Phillips’ penalty before the Serbian side pulled another one back in stoppage time through Aleksandar Katai, but it was not enough to stop City from picking up a maximum haul of 18 points.

Benjamin Sesko and Emil Forsberg struck twice in five second-half minutes to earn already qualified RB Leipzig a 2-1 victory over Young Boys. Ebrima Colley briefly levelled for the Swiss outfit.

Celtic picked up their first victory of the group-stage campaign thanks to Gustaf Lagerbielke’s late strike to give them a 2-1 win over Feyenoord at Celtic Park.

Luis Palma opened the scoring for Celtic just after the half-hour mark, but they thought they would remain winless in the competition when Feyenoord pulled level through Yankuba Minteh. However, Celtic snatched the win in stoppage time when Lagerbielke nodded in from close range.

Strikes from Antoine Griezmann and Samuel Lino handed Atletico a 2-0 win over Lazio after both sides had already secured their place in the last 16 from Group E.

Porto progressed through to the last 16 of the Champions League with a 5-3 win over Shakhtar Donetsk.

Porto hit the front in the ninth minute when Galeno opened the scoring. Danylo Sikan equalised on the half-hour mark, only for Galeno to grab a second to give the hosts a 2-1 lead at the break.

The Portuguese side doubled their advantage when Mehdi Taremi lashed into the roof of the net, but Shakhtar hit back through Stephen Eustakio’s own goal.

Porto sealed victory in the 76th minute when Pepe stabbed home and added another through Francisco Conceicao before Eguinaldo knocked in a late consolation for the Ukrainian team.

Royal Antwerp grabbed their first victory in the Champions League this season with a dramatic 3-2 triumph over Barcelona.

The Belgian side hit the front in the second minute when Arthur Vermeeren slammed home from close range, however, Barca were on level terms 10 minutes before the break through Ferran Torres.

The hosts regained their advantage with a goal from Vincent Janssen, but Barcelona thought they nicked a point thanks to Marc Gulu’s strike in the first minute of stoppage time.

But Antwerp hit a dramatic winner when George Ilenikhena struck a minute later.

Warren Zaire-Emery’s second-half strike salvaged a 1-1 draw for Paris St Germain at Borussia Dortmund to ensure his side advanced to the Champions League last 16 as Group F runners-up.

A wild first half at Signal Iduna Park, where the hosts secured top spot in the group, somehow ended goalless after what felt like an unending stream of missed chances for both sides.

Dortmund, who had already qualified, finally took the lead via Karim Adeyemi after the break, when results elsewhere also began to swing in PSG’s favour.

It was not long before 17-year-old Zaire-Emery opened his Champions League account just when it mattered most to book PSG a trip to the knockouts, becoming the youngest French goalscorer in the history of the competition.

The missed opportunities started early, Zaire-Emery scuffing a close-range effort and Vitinha missing from 25 yards after Marco Reus had tested his luck from a similar distance for the hosts moments earlier.

Marius Wolf was in a good position to open the scoring but instead succumbed to pressure from Lucas Hernandez’s well-timed tackle, and the Germans were fortunate when Kang-In Lee missed a golden opportunity from six yards, though Randal Kolo Muani might have been offside in the build-up.

PSG looked certain to take the lead when Kylian Mbappe rounded Gregor Kobel and found himself facing an open net, but Niklas Sule scrambled in for an incredible clearance on the goal-line to preserve the deadlock, which remained intact after Bradley Barcola curled an effort off the post and Kolo Muani poked wide despite finding himself through on goal.

Gianluigi Donnarumma was also kept busy, denying Reus and Salih Ozcan as the half somehow marched to a close without a goal after Kobel denied Kolo Muani and Mats Hummels headed into the side-netting with the final touch before the break.

Lee fired directly into Kobel’s awaiting arms after the restart as PSG desperately looked for a way to avoid an unceremonious exit, but instead gave the ball away at the edge of their own area, with Dortmund eventually working it to Adeyemi, who slotted the opener past the keeper after 51 minutes.

It took just five minutes for Zaire-Emery to issue a reply via a slight deflection through Adeyemi’s legs and over the hand of an outstretched Kobel, while Donnarumma denied Donyell Malen just after the hour mark.

PSG were hungry for another but instead saw Ramy Bensebaini first clear away Kolo Muani’s chance to head home, then Mbappe fired just wide of the right post.

He thought he had turned the contest on its head when he put the ball in the back of the net in the 76th minute, but referee Glenn Nyberg turned to VAR Dennis Higler and, with semi-automated offside tech in play, ruled out the would-be winner.

Soon word seemed to spread amongst the visitors that a draw would be enough to see them through, and while Dortmund at times looked keen to challenge for another both sides were satisfied to split the points.

Barcelona finished on top of Champions League Group H despite slipping to a shock 3-2 defeat to Royal Antwerp in a dramatic contest at the Bosuilstadion.

After the first half had seen Arthur Vermeeren’s early effort for the hosts cancelled out by Ferran Torres, former Tottenham striker Vincent Janssen restored the lead for Mark van Bommel’s Antwerp 11 minutes after the break.

Barcelona then hit back via Marc Guiu in stoppage time, only for George Ilenikhena to reply moments later to wrap up a historic win for the Belgians, who had lost each of their previous five games in what was their debut Champions League group campaign.

Barca had gone into the match with qualification for the last 16 secure, and retained top spot ahead of Porto – who beat Shakhtar Donetsk 5-3 – thanks to a superior head to head record.

It was the second time in four days that Xavi’s men were beaten, following Sunday’s 4-2 LaLiga loss at home to Girona.

With a starting XI showing seven changes from that game, Barcelona found themselves a goal down in the second minute when a mistake at the back was punished by 18-year-old midfielder Vermeeren.

Receiving a pass from goalkeeper Inaki Pena in the Barca box, Oriel Romeu inadvertently diverted the ball to Vermeeren, who fired into the net.

Janssen then saw his shot on the turn comfortably dealt with by Pena, and sent a further effort off target.

Having struggled for rhythm, Barca were then back on level terms in the 35th minute via a counter-attack that ended with Lamine Yamal playing a fine pass and Torres sweeping the ball past Jean Butez.

Antwerp had the ball in the net again five minutes into the second half but Janssen’s finish was disallowed for handball, and Yamal struck the bar at the other end moments later.

A dramatic few minutes then continued with Barca’s Sergi Roberto being shown a red card for a challenge on Mandela Keita before the decision was overturned via VAR, before Antwerp did regain the lead.

Romeu was again guilty of sloppiness, being dispossessed near his box by Alhassan Yusuf, and he laid the ball to Janssen, who struck into the corner of the net.

Xavi responded with a triple substitution on the hour as Ilkay Gundogan, replacing Romeu, Joao Cancelo and Pedri came on.

Further Antwerp pressure saw Chidera Ejuke put a shot from distance over and Soumaila Coulibaly head wide, either side of a Pedri attempt being blocked.

Barca pushed to hit back late on and equalised in the first minute of stoppage time when Guiu, who had come on for Robert Lewandowski, headed in a Gundogan free-kick.

But one of Antwerp’s substitutes then had the final say as Ilenikhena – Guiu’s fellow 17-year-old – beat Pena a minute later to seal a famous result.

Gustaf Lagerbielke was the unlikely hero as Celtic finally ended their long wait for a Champions League win amid late drama in their dead rubber against Feyenoord at Parkhead.

Luis Palma’s 33rd-minute penalty put the home side on track after the impressive Liam Scales had been brought down, but the Dutch champions levelled through Yankuba Minteh in the 82nd minute.

However, substitute Lagerbielke headed home his first Celtic goal in stoppage time on his first appearance since September to earn a 2-1 victory. The Sweden centre-back nodded in from close range following Matt O’Riley’s exquisite cross as Celtic maintained pressure following a corner.

It was Celtic’s first Champions League group stage win in 16 matches since they beat Anderlecht six years ago during Brendan Rodgers’ first spell in charge and their first at home since defeating Ajax in October 2013.

The dramatic finale livened up a previously flat home support and ensured Group E bottom side Celtic doubled last year’s two-point tally.

Stephen Welsh was in the Celtic line-up for the first time since he suffered an ankle injury four months ago, while Kyogo Furuhashi started after two substitute appearances.

Mikey Johnston and Tomoki Iwata were handed their third starts in a row, but the Japanese midfielder only lasted 19 minutes before injury forced him off for Paulo Bernardo.

Feyenoord could not finish above third place and they made five changes. Their supporters were out in full force with several pockets of away fans evident in home sections.

With the vocal Green Brigade group still banned by Celtic and nothing at stake, the visitors from Rotterdam highlighted the lack of atmosphere among their hosts with chants including ‘Shall we sing a song for you?’

Both sides got in behind in the opening quarter. Furuhashi was denied by a good stop from Justin Biljow after being played through by Scales. Santiago Jimenez was then flagged offside after rounding Joe Hart and netting, before the goalkeeper produced a diving save after the Mexico striker burst on to a long ball.

Celtic got the breakthrough when Ramiz Zerrouki pulled down Scales as Feyenoord defended a corner. The visitors protested vehemently, but French referee Benoit Batien had not needed VAR to spot the offence and replays backed his decision. Palma kept his cool to convert after the furore.

Celtic survived several scares before the break. Hart made another excellent save just before Callum McGregor cleared off the line, and Lutsharel Geertruida hit a post from close range after Feyenoord cut the Hoops defence open.

Palma had an excellent opportunity to double his tally early in the second half after Alistair Johnston’s low cross found its way to the back post, but Biljow saved with his foot.

Hart made another two decent stops before Celtic got greater control on proceedings.

Rodgers brought on summer signing Lagerbielke for Welsh and 17-year-old left-back Mitchel Frame made his debut on the wing after Palma suffered a facial knock and went off in the 75th minute.

The visitors levelled when the ball broke for Minteh in the left channel and the substitute had time and space to fire home from 10 yards.

Two Hart saves and a Scales block prevented Celtic from falling behind before McGregor struck the crossbar from 30 yards.

It looked like another late hard luck story for Celtic until Lagerbielke’s winner sparked jubilation with several supporters running on to the pitch to celebrate. One sparked an angry response from Rodgers as the manager ran up the touchline to berate the fan as he was led away by stewards.

A Hart save and a Johnston block maintained Celtic’s lead before another goalmouth scramble preceded the final whistle.

Samuel Chukwueze came off the bench to end Newcastle’s Champions League adventure as AC Milan fought back from a goal down to win at St James’ Park.

On a night when both sides needed to win to stand any chance of progressing, goals from Christian Pulisic and Chukwueze handed the Serie A side a 2-1 victory which was not enough to prolong their involvement in the competition following a 1-1 draw between Borussia Dortmund and Paris St Germain in Germany.

Seven-time winners Milan at least have the consolation of a Europa League berth while Eddie Howe’s men, who took a 33rd-minute lead through Joelinton’s piledriver in front of a crowd of 52,037, slipped out of Europe all together after finishing bottom of Group F in their first campaign since 2002-03.

Goalkeeper Martin Dubravka shook off a bout of illness which had threatened his participation to retain his place in the team with striker Callum Wilson making his first start since damaging a hamstring during the 2-0 defeat at Dortmund on November 7.

Such have been head coach Howe’s selection problems that only four of the men who started the reverse fixture in September – Kieran Trippier, Fabian Schar, Bruno Guimaraes and Anthony Gordon – did so on Tyneside.

St James’ reverberated as an expectant home crowd played its part, and Gordon’s early challenge on full-back Davide Calabria was cheered almost as appreciatively as a goal on a night when the stakes could hardly have been higher.

Trippier curled a sixth-minute free-kick over Mike Maignan’s crossbar after Pulisic had bundled Gordon to the ground as the Magpies maintained their early intensity, although the visitors with experienced striker Olivier Giroud providing a focal point, gradually eased their way into the game.

For all their dominance, Newcastle were struggling to create meaningful chances and Schar’s speculative 18th-minute strike from distance, which sailed high over Maignan’s crossbar, had a touch of impatience about it.

However, Fikayo Tomori had to make a superbly-timed intervention on his own line to prevent Miguel Almiron from converting Joelinton’s cross two minutes later.

Rafael Leao whipped a shot wide of Dubravka’s left post after Yunus Musah had surged deep into enemy territory to feed him as the visitors responded, but Maignan had to pluck Almiron’s goal-bound header from under his crossbar after he had met Joelinton’s inviting cross.

But it was the Brazilian who broke the deadlock when he ran on to Lewis Miley’s lay-off and smashed a right-footed shot past the helpless Maignan and into the top corner before sprinting to the sideline to celebrate with Howe and assistant Jason Tindall as the stadium erupted.

The game descended into a scrappy affair with both sides struggling to retain possession as the half-time whistle approached, and it was the Magpies who ultimately headed for the dressing rooms much the happier.

Wilson picked out the keeper with two attempts and Gordon fired over from another with Newcastle looking to kill the game off as news that Dortmund had scored rippled around the stadium.

PSG’s equaliser minutes later did little to quell the atmosphere, but spirits dropped with 59 minutes gone when the home defence failed to deal with Leao’s left-wing cross and Giroud teed up former Chelsea midfielder Pulisic to level from close range.

A much-improved Milan were causing significantly more problems with Leao in particular a persistent threat, but substitute Alexander Isak sent a dipping shot over with 23 minutes remaining and Maignan had to make a superb save to tip Guimaraes’ drive on to his crossbar two minutes later.

The woodwork came to Newcastle’s rescue 11 minutes from time when Leao’s shot came back off the post after Tino Livramento’s error had sparked a pacy counter-attack, but there was no escape five minutes later when Noah Okafor and Luka Jovic combined to set up fellow substitute Chukwueze to win it.

Former ballboy Micah Hamilton and fellow youngster Oscar Bobb struck as a much-changed Manchester City ended the Champions League group stage with a 3-2 win at Red Star Belgrade.

Kalvin Phillips also joined the two 20-year-olds on the scoresheet with a late penalty after manager Pep Guardiola rotated his squad for the Group G dead rubber at the Rajko Mitic Stadium.

Manchester-born academy product Hamilton marked his debut with a superb strike in the 19th minute before Norwegian Bobb, filling in for compatriot Erling Haaland up front, added the second after 62 minutes.

Hwang In-beom pulled one back but Phillips gave City breathing space with his first goal for the club after a foul on Hamilton before Aleksandar Katai headed a late home consolation.

The result meant holders City, who had already secured top spot, finished the group phase with a maximum haul of 18 points while winless Red Star ended bottom.

With City facing Crystal Palace before travelling to Saudi Arabia for the Club World Cup next week, Guardiola not only gave chances to Hamilton and Bobb but brought in fringe players such as Stefan Ortega and Phillips.

In all he made nine changes and, initially, intensity was lacking as Red Star carved out the first opportunity with Osman Bukari’s shot being blocked by John Stones.

Yet City still controlled most of the possession and Hamilton took full advantage of their first serious attack.

Jack Grealish picked out Matheus Nunes and the Portuguese prodded on for Hamilton, cutting inside from the right, to take up the attack.

Hamilton raced into the area and beat Red Star captain Aleksandar Dragovic on the outside before lashing a shot into the top corner from a tight angle.

The hosts responded with Kosta Nedeljkovic turning inside the box and curling narrowly over but City threatened again as Bobb had an effort blocked.

Hamilton almost created another goal for Bobb when he fired in a dangerous low ball from the right but the latter could not make contact at the far post. Phillips, making a rare start, then shot wide.

Hamilton went close again early in the second half when he curled a low effort just wide but City needed Ortega to keep them level.

The German first produced a good reaction save to keep out a Cherif Ndiaye volley at close range and then pushed away a firm strike from distance from Guelor Kanga.

Bobb then took centre stage as he doubled City’s lead just after the hour. He picked up possession from Rico Lewis and opted against the return pass, instead wrong-footing the defenders with a weaving run and sliding a low finish inside the far post.

Red Star rallied and, after Jovan Mijatovic hit the post, Hwang beat Ortega with a low strike to reduce the deficit after linking up with Bukari.

Yet Phillips made no mistake from the spot five minutes from time after Hamilton was brought down by Nasser Djiga and that proved decisive as Katai headed a second Red Star goal in stoppage time.

Jonny Evans was left to reflect on what might have been for Erik ten Hag’s stumbling Manchester United at the end of a miserable European campaign, with a “massive day” against rivals Liverpool now looming large.

Boos echoed around Old Trafford for a second straight match as Saturday’s 3-0 Premier League humbling at the hands of Bournemouth was followed by a meek 1-0 loss to Bayern Munich.

Tuesday’s lifeless defeat confirmed United’s place at the bottom of a Champions League group many expected them to progress from, meaning they also missed out on a Europa League spot.

The manner of the Red Devils’ European exit increases the spotlight on underfire boss Ten Hag and leaves the side kicking themselves over the mistakes that cost them dearly in Group A.

“You expect to get out of every group being Man United,” deflated defender Evans said after the match.

“I think we made it difficult for ourselves and to go into the last game needing to win and a result to go your way in the other side, the probability of that’s very small.

“Obviously tonight playing against a good Bayern side and once they got the goal it was it was difficult then.”

A paltry four points from five Group A games meant United needed to beat Bayern and hope there was a draw between Copenhagen and Galatasaray to progress in the Champions League.

Asked if it was any consolation that the Danes’ 1-0 victory meant United would only have been able to reach the Europa League had they won anyway, Evans told beIN SPORTS: “I suppose because, I mean, if the result had gone the other way you can kick yourself.

“But, you know, on the flip side of that, I felt like we give absolutely everything tonight. It wasn’t a case of, you know, we could look back…

“Not many chances for either side. They got their one chance and took it.

“It was a very even game but probably whoever got the first goal (was key) and they got it and that’s the way it went.”

United managed the game well in the early stages, restricting Bayern to half-chances in an opening period that ended with Harry Maguire and Luke Shaw picking up injuries.

Evans came on as part of the enforced defensive reshuffle and did a solid enough job, but there was barely anything in terms of threat at the other end.

United managed just one shot on target in what was a must-win match, having blown leads in the 4-3 defeat at Copenhagen and 3-3 draw away to Galatasaray.

Asked if United could have done more in the previous games to avoid facing such a predicament in the group finale, Evans said: “Of course.

“There’s six games. To be able to get down to the last game, we’re sitting bottom of the group going into the match.

“The two away games, especially Copenhagen and Galatasaray, were big moments in the group where we felt like we probably slipped up a little bit and made it more difficult for ourselves tonight.”

United players looked drained as they left Old Trafford, where no players stopped to speak to non-rights holders in the mixed zone and face questions about their 12th loss in all competitions of the campaign.

Some took a shortcut to avoid walking through the interview area. Even in-house broadcaster MUTV did not get to speak to a player.

United fans will be hoping their players instead do their talking on the pitch against bitter foes Liverpool this Sunday as they return to Anfield for the first time since March’s 7-0 annihilation.

Skipper Bruno Fernandes is suspended for a match that Ten Hag’s side head into without a string of injured players, increasing the incline on what already looked to be an uphill battle.

“Massive day for the club, you know, away at Anfield,” homegrown defender Evans said.

“We’ve got a couple of days now between the game and you’ve got to dust ourselves down. We’ve got a big match, a huge match.

“I’m sure in the next day or two once the feeling of this match sort of passes by, we’ll only be excited leading up to that game.”