Rangers' slim hopes of playing Europa League football in the new year are all but over following a 3-0 defeat to Napoli in Naples, heaping further pressure upon Giovanni van Bronckhorst.

The Scottish side needed a result and a favour from Liverpool against Ajax to retain a realistic chance of finishing third, and while Jurgen Klopp's side did their part, Rangers were swept aside by the Serie A leaders.

Napoli took the lead after just 11 minutes, Giovanni Simeone rifling home after Giovanni Di Lorenzo teed him up, and the forward was on the scoresheet again five minutes later as he tucked home Mario Rui's cross.

Tanguy Ndombele's fierce strike from outside the box clattered off the bar before the break, while the second half saw Alfredo Morelos fail to connect from close range in the visitors' best chance of the game.

Any hope of a late comeback was crushed 10 minutes from the final whistle when Leo Ostigard was left unmarked and headed home Giacomo Raspadori's corner.

With Rangers three points behind Ajax and having lost their first meeting 4-0, Van Bronckhorst's side need a remarkable result in Amsterdam next week to clinch third place and Europa League football.

Bayern Munich eased to a 3-0 win to compound a miserable day for Barcelona as they were eliminated from the Champions League at the group stage for a second successive season.

Inter's 4-0 win against Viktoria Plzen earlier on Wednesday had already sealed Barca's fate, which led to a sombre mood from the first whistle at Camp Nou.

First-half goals from Sadio Mane and Eric Maxim Choupo-Moting were followed by a Benjamin Pavard strike with the last kick of the game.

Bayern were already through from Group C but confirmed themselves as group winners ahead of Inter with this win, with Barca dropping into the Europa League.

2 - #FCBarcelona has been eliminated of UEFA Champions League #UCL group stage in back-to-back seasons, something that had not happened since the 1997-98 and 1998-99 campaings under Louis Van Gaal. Disappointment. pic.twitter.com/GkcqNp2Ncq

It took just 10 minutes for Bayern to strike after Serge Gnabry played a ball through to Mane, who outpaced Hector Bellerin before calmly dinking the ball past Marc-Andre ter Stegen.

The second also came thanks to an assured pass from Gnabry as Bayern countered and Choupo-Moting was slipped in on the right of the penalty area, firing his shot through the legs of Ter Stegen just after the half-hour mark.

The hosts thought they had a penalty just before half-time when referee Anthony Taylor pointed to the spot after Robert Lewandowski was felled by Matthijs de Ligt, but a VAR check revealed the Dutch centre-back got a touch on the ball before any contact was made with the former Bayern man.

Gnabry had the ball in the net with a terrific left-foot finish to Ter Stegen's right 10 minutes into the second half, yet his effort was ruled out for offside.

A game that had the feeling of a dead rubber fizzled out, with Lewandowski and Co. never looking like getting back into the game before Gnabry had his third assist of the night as his volley from a corner found Pavard at the far post for a tap-in.

Mohamed Salah continued his Champions League scoring run as Liverpool sealed their place in the knockout stages with a 3-0 triumph at Ajax.

Jurgen Klopp has now progressed from six consecutive group stages in the competition with Liverpool, a club-record run, after the Reds dominated on Wednesday in Amsterdam.

Salah scored his sixth goal in his last four Champions League games with a 42nd-minute opener, before Darwin Nunez and Harvey Elliott added quickfire second-half finishes to seal victory.

Ajax will drop into the Europa League by avoiding a resounding defeat at winless Rangers on matchday six, while Liverpool must beat leaders Napoli by an unlikely four goals to win Group A.

Ajax should have taken a third-minute lead but Steven Berghuis struck a gilt-edged opportunity against the right post, with the midfielder curling narrowly wide shortly after.

A resolute Liverpool continued with their backs against the wall before Andy Robertson smashed a rare Reds chance just off target, but Klopp's visitors soon hit the front.

Jordan Henderson delicately chipped through for Salah to neatly lift over the onrushing Remko Pasveer, before Nunez inexplicably smashed the left post with the goal gaping two minutes later.

Nunez made amends after the interval, heading Robertson's corner in off the right post before Elliott fired into the roof of the net two minutes later.

Substitute Kenneth Taylor blasted a presentable opportunity over after the hour mark, though Ajax never threatened an unlikely comeback.

What does it mean? Reds continue Ajax hot streak to qualify with ease

Underwhelming returns in the Premier League thus far have led to scrutiny for Liverpool, though the Reds emphatically delivered in what was their 150th match in the Champions League.

Klopp will take encouragement from the Reds' fourth straight victory in the competition over Ajax – only Real Madrid (seven) have managed a longer such streak – leaving Alfred Schreuder with much to ponder.

Ajax, whose first-half dominance failed to pay dividends, will likely settle for a Europa League place after falling to a seventh loss in nine home games against English sides in Europe.

Super Salah

Salah may be yet to hit his usual heights in the Premier League, but the forward collected his 42nd goal in the Champions League – only Didier Drogba (44) has more among African players.

The Egypt international presented a constant threat on the right flank, scoring in a fourth straight game in the competition for just the second time, as well as assisting Elliott for the third goal.

Bad from Berghuis

Berghuis was left to rue his two early missed chances, the first of those a routine finish that the midfielder would have been expected to slot past Alisson and into the back of the net. 

Those errant efforts summarised a frustrating outing for Ajax, who started in dominant fashion but faded away rapidly after Salah's first-half opener.

What's next?

Liverpool host Premier League strugglers Leeds United on Sunday, while Ajax are not in action until their final Champions League game at Rangers on Tuesday.

Inter confirmed their place in the knockout stages of the Champions League and simultaneously eliminated Barcelona after cruising to an Edin Dzeko-led 4-0 win over Viktoria Plzen.

The Nerazzurri knew they would be through regardless if Barcelona failed to win later in the day at home to Bayern Munich, but Simone Inzaghi's men removed all doubt with a professional display.

Initially there were hints of nervousness when Inter spurned a couple of first-half opportunities, but Henrikh Mkhitaryan gave them the breakthrough before Dzeko ensured it was effectively game over – for Plzen and Barcelona – by half-time.

A clinical Dzeko finish just past the hour was then added to by a late Romelu Lukaku strike on his return from injury as Inter eased into the next round.

Inter's persistence paid off in the 35th minute following a frustrating first half-hour.

Alessandro Bastoni charged up the left and crossed after a one-two with Federico Dimarco, and Mkhitaryan was on hand to nod in at the back post.

Dzeko ducking out of the way proved crucial to Mkhitaryan getting that opportunity, though the Bosnian did not have to wait long for a goal of his own.

Dimarco latched on to Nicolo Barella's exquisite long-range pass and played a first-time ball into the danger zone for Dzeko to tap home close to half-time.

Mkhitaryan nearly added a spectacular second just after the break, his 25-yard effort clipping the outside of the post.

But Dzeko did double his tally, guiding a controlled left-footed effort into the bottom-left corner from the centre of the box following good work by Lautaro Martinez.

Substitute Lukaku then found the same corner in the 87th minute with an emphatic finish after two months out.

Liverpool can seal progression to the Champions League last 16 when they play on Wednesday, but Barcelona could see their exit confirmed from Europe's top competition.

Jurgen Klopp's Reds make the trip to face Ajax in Group A knowing they are guaranteed a spot in the Europa League at the very least – and simply avoiding defeat would guarantee their place in the Champions League knockout stages.

It is a more dicey affair for Xavi's Barca, however, as they welcome Bayern Munich to Camp Nou in Group C knowing a loss would spell the end of their journey. Even a win will not be enough if Inter defeat Viktoria Plzen.

Tottenham will hope to keep their noses in front in Group D, with Marseille and Sporting CP just a point behind, while Atletico Madrid have work to do in Group B.

Stats Perform previews Wednesday's eight matches by picking through the Opta data.

Ajax v Liverpool

Ajax have made for generous opponents for Liverpool of late, losing their last three against the Reds in the Champions League. Only Juventus (four, 1997-2004) and Real Madrid (seven, 2010-2019) have previously won four in a row against Ajax in the European Cup or Champions League.

Yet Ajax remain the last Dutch side to achieve a home win against Liverpool, albeit that was back in 1966, with the Premier League side unbeaten in seven subsequent trips to the Netherlands.

Liverpool's countrymen have also made hay, as Ajax have won just one of their last eight home European matches against English teams, beating Manchester City in October 2012.

With or without another strong result, this will be an historic occasion for Liverpool and Klopp, who will match Rafael Benitez's 62 Champions League matches in charge of the Reds, who bring up 150 games in the competition.

Barcelona v Bayern Munich

Needing a win, Barca might have hoped to face any team but Bayern, who have a record three Champions League away wins at the Blaugrana. Along with Juventus and Real Madrid, they are one of three teams to have won more matches at Barca than they have lost.

Home and away, Barca have lost nine of their 12 Champions League matches against Bayern, including the past five in a row.

In fact, if Bayern win again, they will match Madrid's record of 10 wins against a single opponent in the competition – Madrid's dominance coming against Bayern.

Although Bayern are already through, they are seeking a fourth home-and-away double against Barca in a Champions League season (also 1998-99, 2012-13 and 2021-22). Dynamo Kyiv (in 1997-98) are the only other team to beat Barca twice in the same campaign even once.

Tottenham Hotspur v Sporting CP

Sporting won 2-0 against Tottenham in Portugal in what was the sides' first meeting, but they have a dismal record in England, with two victories in 15 attempts away to English sides.

Spurs have won six of their seven home European matches against Portuguese opposition, only losing to Benfica in the 2013-14 Europa League.

Both of Tottenham's wins in this campaign have come at home, where Antonio Conte is bidding to become just the second Spurs coach to win each of his first three at home in the Champions League – after Harry Redknapp.

He and Tottenham will know they must keep their focus early and late; Sporting's last three Champions League goals have come in either the first or last minutes of the match, netting twice in second-half stoppage time in the reverse fixture.

Atletico Madrid v Bayer Leverkusen

Atletico have not lost at home to Leverkusen in their prior four such matches, winning two and drawing two, but the Bundesliga team have started to turn the tide, winning two in a row against them in the Champions League.

That strong home record applies whenever Atletico face German opposition, though, as Borussia Dortmund were the last Bundesliga visitors to win there in 1996. Atleti are unbeaten in 11 since.

Diego Simeone needs his team to rediscover their scoring touch, having gone three without a goal in the Champions League.

That is their worst run under Simeone. Only once in the competition have Atletico gone four without netting, back in 2009 under Abel Resino.

Other fixtures:

Club Brugge v Porto

21 – Club Brugge goalkeeper Simon Mignolet has saved all 21 of the shots on target he has faced in the Champions League this season. He has prevented a competition-leading 4.9 goals, according to expected goals on target data.

4 – Four of Porto's last seven Champions League goals have come from the penalty spot.

Inter v Viktoria Plzen

12 – Inter have scored 12 of their last 14 Champions League goals in the second halves of matches. All three against Barca last time out came after the interval – only the third time an away team has netted three second-half goals at Camp Nou in this competition.

28 – Plzen have averaged just 28 per cent of the possession in the Champions League this season, the lowest average by a team in a single season since Opta data collection began in 2003-04.

Napoli v Rangers

4 – Napoli have won all four of their matches in the Champions League this season and could become the first Italian side to win their opening five games in a single campaign since Juventus in 2004-05. 

12 – No goalkeeper has faced more shots on target (29) or conceded more goals (12) than Rangers' Allan McGregor in the Champions League this season. Indeed, he has only kept four clean sheets in 21 appearances in the competition overall.

Eintracht Frankfurt v Marseille

50 – Eintracht Frankfurt's Mario Gotze could make his 50th start in the Champions League in this match. He has been involved in 25 goals in his previous 65 appearances, including 21 in his 49 starts.

3 – Marseille have won their last two games in the Champions League – both against Sporting CP – and will be looking to win three in a row for the first time since October-December 2010, when they won four on the spin under Didier Deschamps.

Chelsea manager Graham Potter praised his side for qualifying for the Champions League last-16 with a game to spare having lost their opener to Dinamo Zagreb.

The Blues booked their ticket for the knockout stages with a 2-1 away win over Salzburg, after impressive strikes from Mateo Kovacic and Kai Havertz in each half, either side of Junior Adamu's goal.

Chelsea had lost their opening game of the group stage, 1-0 at Dinamo Zagreb, leading to Thomas Tuchel's dismissal, but under Potter have bounced back with 10 points from four games, including strong away wins at Milan and Salzburg, securing top spot in Group E.

"Very [satisfied]. It’s not easy to win here as you can see from the record they have and the quality of the team," Potter told reporters.

"We had to play well and I thought we did. We created some good chances in the first half and were unlucky not to go more than 1-0 up.

"Then one action, with the quality at this level, and it’s 1-1. I thought our response was really good then, so I am delighted to go through, delighted with the performance of the players. I thought they were fantastic tonight.

"To go through with a game to spare is brilliant considering where we started the competition."

Havertz's 64th-minute winner was a spectacular left-foot strike that cannoned in off the crossbar.

The goal was the German's first this season in the Champions League, and third in all competitions. It was also Havertz's first goal away from Stamford Bridge for the Blues since April.

"His quality is there; he’s an incredibly talented player," Potter said. "He’s been nearly there and obviously, scoring a goal like that is bound to help.

"I wouldn’t be able to score a goal like that to be fair, I can only imagine. It’s a fantastic strike and an indication of the quality he has, so I’m really pleased for him."

Potter brushed off concerns about his side's wastefulness in front of goal, having had 15 shots, including 11 on target, while he hinted they may rotate their squad for their final group game against Dinamo having already qualified.

The Blues take on Potter's former club Brighton and Hove Albion on Saturday, followed by Dinamo (November 2), Arsenal in the Premier League (November 6) and Manchester City in the EFL Cup (November 9) in quick succession.

"We're at home at Stamford Bridge [against Dinamo] and we'll try our very best," he said. "We want to win every game we play, that is the mentality we have to have.

"But clearly, we have a game at the weekend and another game the weekend after, so maybe we can rotate a little bit. But we will try our best."

Massimiliano Allegri rued Juventus' previous Champions League shortcomings after Tuesday's 4-3 defeat at Benfica condemned them to their first group-stage exit since 2013-14.

Juventus travelled to the Estadio da Luz knowing only a victory would keep them in contention for a top-two finish in Group C, but were left stunned by a scintillating performance from Benfica.

Rafa Silva's double, as well as goals from Antonio Silva and Joao Mario, saw Benfica establish a 4-1 lead after 50 minutes, and the hosts stood firm when Juventus responded through Arkadiusz Milik and Weston McKennie late on.

A 2-0 defeat at Maccabi Haifa earlier this month left Juventus needing maximum points from their final two games to have any hope of progressing, and Allegri believes their Champions League fate was all but sealed before their trip to Portugal.

"We are sorry and angry, but the elimination did not come today, but in the previous games," Allegri said.

"It is not necessary to get down, we would not want these things to happen, but they do happen. 

"There must be a path of growth. Unfortunately, we conceded a goal from a penalty for 2-1, then you saw the match. We must continue to work."

Juventus made several unwanted pieces of history at Benfica, conceding three first-half goals for the first time in a Champions League game and losing a fourth match in a single group-stage campaign for their first time ever. 

The Bianconeri are also 10 points adrift of the Serie A summit following an underwhelming start to their domestic season, and speculation regarding Allegri's future is sure to intensify following Tuesday's loss.

However, the Juventus boss chose to remain philosophical after their exit, challenging his team to respond with a renewed run of league form.

"Failure? No. These evenings happen, defeats happen. It must be an opportunity to dive back into the championship," Allegri added.

"You fall to get back up. I would have liked to have played the last game with Paris Saint-Germain to force Benfica out. The reality is this, let's focus on the future. 

"We have to react, we have a championship to play, there is a Europa League to win. It will not easy, there are players to recover. From tomorrow, we just need to get back to work.

"The first part of the season was more difficult than expected but we have 20 days to do well, then at the [World Cup] break we will recover almost all the players."

Paris Saint-Germain will not win the Champions League because they are "terrible at defending," according to former Manchester United goalkeeper Peter Schmeichel.

Kylian Mbappe and Lionel Messi scored twice while Neymar was also on target in the thumping 7-2 victory over Maccabi Haifa at Parc des Princes. 

Despite progressing to the knockout stages with a match to spare, the Champions League trophy has remained elusive to PSG, who are yet to register a clean sheet in this season's competition after Abdoulaye Seck's brace for the visitors.

Schmeichel, who lifted the trophy with United in 1999, heaped praise on the attacking trio of Mbappe, Messi and Neymar after another devastating goalscoring display, but believes that defensive frailties will wreck any title ambitions.

"What was special about this game was the quality of the goals," he told CBS Sports Golazo. "You can't defend against that. These three guys up front, Mbappe, Neymar and Messi, when they play like that, there are no answers.

"I'm not sure when you talk about them winning the Champions League. I think the problem they have also showed today. When they're 3-0 up, all of a sudden, it's 4-2. They need to score a lot of goals to win games, and it's not always going to happen.

"I think they are terrible defending; that's also because of the three front players. When you are at the stadium, and you see how little they take part in defending.

"Everybody else, Bayern Munich, Manchester City, all those teams, it's 11 players attacking, it's 11 players defending. I think in modern-day football, that's what you need.

"That could be the problem in one game, one game against Man City, one game against Real Madrid, it's enough to get knocked out."

Fabio Capello described it as "a serious blow" as Juventus were knocked out of the Champions League before the knock-out phase.

The former Juventus, Roma and Milan head coach said Massimiliano Allegri's team lacked spirit and fight as they went down 4-3 at Benfica, with two late goals for the Italians serving only as pitiful consolation.

Juventus, who have just one win from five games, could yet finish bottom of Group H, as their last opponents are mighty Paris Saint-Germain who are battling with Benfica for top spot.

Should Juventus lose that one, and Maccabi Haifa take even a point from their home game with Benfica, the Turin giants will sink to fourth place and miss out on the Europa League.

Speaking on Italian channel Sky Sport, Capello said: "Allegri lacked the players on whom he founded this team, but they did not show character and determination.

"Even if they do not have these players, they must always demonstrate who Juve are, a team that never give up, want to fight, and tonight they didn't show themselves as they have in the past."

Capello added, according to Tuttosport: "This is a serious blow, you have to start from this moment with everyone together. I don't seem to see this spirit."

The 76-year-old, who also coached England, Russia and Real Madrid in his storied career, said Juventus were simply sluggish compared to the pace they need to play at.

"Juve are always under pace even when they win in the league," Capello said. "They win because at that moment they have better players than the opponents. When they have found players of equal or superior quality, this is the result."

Juventus will be absent from the last-16 stage for the first time since the 2013-14 season, and their points tally is the lowest they have managed after five games of any previous Champions League campaign where they have featured.

Capello found praise for teenage substitutes Samuel Iling and Fabio Miretti, however, commending them for showing purpose and quality.

"At this point, Juve must think about recovering in the league," Capello said, with Juventus sitting eighth in Serie A, "but they have players who may be ready for the future."

Thierry Henry feels Juventus have issues "from top to bottom" and sacking Massimiliano Allegri will not change their fortunes.

A 4-3 defeat to Benfica on Tuesday saw Juve crash out of the Champions League, while they will exit European competition entirely if Maccabi Haifa better their result in the final round of group-stage matches.

The Bianconeri's loss in Lisbon was their third in five games across all competitions, with Allegri's side down in eighth in Serie A and already 10 points behind leaders Napoli.

Juve's first group-stage elimination in the Champions League since 2013-14 increased pressure on Allegri, but former Bianconeri striker Henry believes replacing the coach will not change their situation.

"I wouldn't go there. As you know, I'm on the other side of the line now, so it is very difficult to call out a manager," he told CBS Sports.

"I think there is a lot of problems from top to bottom; it is not only at the bottom and on the field where things are not going well.

"I said it when [Andrea] Pirlo left, I said it when [Maurizio] Sarri left, he is not a bad coach.

"What is going on behind closed doors, we don't know. It takes time sometimes. It's not that if you just bring in Allegri, it is going to work.

"Where are you going to go? What is going to be the plan? Who are you going to bring in? You need to let people work for a little while to make change, to change who is going to leave, who is going to come and play in this system.

"We've seen it with [Mikel] Arteta [at Arsenal]; it took him two years to put a decent team on the field, and people were having a go.

"Are you going to stay with the man or are you not? Think about it carefully. They thought that bringing him [Allegri] in, things were going to change, and it hasn't happened yet."

Stefano Pioli will set his Milan side out to qualify for the Champions League round of 16 in style by beating Salzburg in a decisive San Siro showdown next week.

The Rossoneri moved above Salzburg into second place in Group E on Tuesday with a 4-0 demolition of Dinamo Zagreb at Stadion Maksimir.

Matteo Gabbia opened the scoring with his first Milan goal, heading in a Sandro Tonali free-kick, and the Serie A champions ran away with it in the second half.

Rafael Leao's solo strike doubled their lead, and Olivier Giroud added a third from the penalty spot before a bizarre Robert Ljubicic own goal completing the scoring, with Dinamo's hopes of qualifying emphatically dashed.

Milan now only need a point to advance along with group winners Chelsea, who beat Salzburg 2-1, but head coach Pioli will not be taking a cautious approach to such a crucial game against the champions of Austria at San Siro next Wednesday.

He said: "Two out of three results are not a double-edged sword. We are not mentally and tactically built to manage, we have to play our best to get the win."

The Rossoneri finished bottom of their group last season, and Pioli believes reaching the last 16 would show the strides they have made.

He added: "I think it is clear that our growth comes from qualification. We have to play with our mentality, and it is the next step, where we would show that we are doing better than last year.

"We must close the discussion next Wednesday without forgetting the championship. We need concentration for the league match against Torino [on Sunday]. Then we will have the time and attention necessary to take care of the next Champions League match in the best possible way."

Pioli praised centre-back Gabbia, who was rock solid at the heart of the Milan defence after coming in to replace the suspended Fikayo Tomori.

"I continue to be convinced of the strength of my group," he said. "I emphasise Matteo's seriousness, but also his skills. He has a sense of position, physicality and skill in aerial duels."

Timo Werner said RB Leipzig could not have played "much better than that" after defeating European champions Real Madrid to keep their Champions League fate in their control.

Werner scored what proved to be the winner in the second half, making it 3-1 after Vinicius Junior had pulled a goal back following first-half strikes from Josko Gvardiol and Christopher Nkunku.

Although Rodrygo netted a late penalty, becoming the youngest Madrid player to score from the spot in the Champions League, Leipzig earned a deserved victory to remain in the hunt for qualification.

Marco Rose's side will progress by avoiding defeat at third-placed Shakhtar Donetsk on the final matchday, and Werner hailed the efforts of his team against the reigning Spanish and European champions.

"I think we performed similar to the first match, but this time we scored! And once we take a lead, it's tough to play us, even for the Champions League winner," the striker said.

"If you lead Madrid by 2-1, you cannot play much better than that. We knew Madrid are strong on the ball and there would be phases where we are pushed back.

"Rose told us to be brave when in possession and that's what we did. Celtic would have done us a big favour by winning, but we still have achieved what we wanted.

"We have it in our own hands [to go through] and don't even need to win against Shakhtar now."

While Werner insisted the memorable victory showed the quality of Leipzig, David Alaba lamented the failings of Madrid, who were without the injured Federico Valverde, Luka Modric and Karim Benzema.

"We were lacking right from kick-off. Leipzig is a team with lots of intensity, very fast in transitions and we went down," the Los Blancos defender said.

"Of course, the players that were missing are very important for our game, real world-class players. Nevertheless, we have the quality to compensate for that and have shown that in the past. We have to do better than this."

Madrid were far from their usual high standards that guided them to domestic and continental glory as they fell to their fourth Champions League defeat in 2022, only in 2001 (five) have they lost more.

However, Carlo Ancelotti's side will still progress as Group F winners as long as they match RB Leipzig's result at Shakhtar Donetsk on the final matchday, when they host Celtic.

Erling Haaland was withdrawn at half-time in Manchester City's Champions League draw with Borussia Dortmund due to a fever and a knock to the foot.

City were held to a 0-0 draw at Signal Iduna Park on Tuesday, with Haaland taken off at the break after an uncharacteristically quiet first half.

Pep Guardiola confirmed after the match that the Norway striker – and Joao Cancelo, who was also brought off at half-time – had been struggling before the game with a minor illness.

Haaland also received a blow to the foot, though Guardiola did not suggest his condition was of major concern, with the striker appearing jovial as he greeted his former Dortmund team-mates on the pitch at full-time.

"Erling didn't feel good, he had a little fever before the game, Joao as well," Guardiola told BT Sport.

"[Haaland] had a knock in the feet. That's why we changed it, and in that period we struggled a lot."

The draw was enough for City to secure their progress as Group G winners, with Dortmund also confirming qualification for the last 16.

However, City should have left with all three points.

Riyad Mahrez won a second-half penalty following a clumsy Emre Can foul but his resulting spot-kick was saved by Gregor Kobel.

That was the 25th occasion of City failing to convert a penalty since Guardiola took over in 2016 (out of a possible 80), more than any other Premier League side over the same period.

"Of course it's a problem. Since I'm here it's 24 or 25 penalties [missed], most of them in the Champions League," Guardiola said.

"It's too much. I always admire the courage, the responsibility [to take a penalty], but of course we miss a lot and it's a problem.

"We have to improve otherwise these little details, these margins in this competition, it's the difference [between success and failure]."

It was also Mahrez's third penalty failure in his past four attempts, though Guardiola is not going to stop him taking future spot-kicks.

"I admire the courage. Riyad, with the last penalties scored a lot last season in important moments, so in that situation I admire the courage," he added.

"If he feels [able] next time he has a penalty, he's going to take it. But of course we have to improve."

Carlo Ancelotti acknowledged "sooner or later" Real Madrid had to lose but Thibaut Courtois lamented Los Blancos' defensive concentration after a 3-2 defeat at RB Leipzig.

Madrid were without the injured Federico Valverde, Karim Benzema and Luka Modric and fell two goals behind after strikes from Josko Gvardiol and Christopher Nkunku on Tuesday.

That marked the first time Madrid conceded twice in the first 20 minutes of a Champions League in a group stage match and just the fourth time in the competition in total.

Vinicius Junior pulled one back and Rodrygo scored a late consolation, but Timo Werner's strike inflicted a fourth Champions League defeat on Madrid in 2022, only in 2001 (five) have they suffered more.

However, Ancelotti refused to criticise Los Blancos – who sit top of LaLiga and remain favourites to win Group F – as he suggested a defeat was expected at some point.

"I'm not angry. It's a defeat, annoying, but it doesn't do much damage," the Madrid coach told Movistar. "Sooner or later it had to happen. Go on, you can't look back.

"I can't criticise a team that has done very well. From defeats, you learn more than ten wins in a row. We are very forceful at set-pieces, but we were not tonight."

Goalkeeper Thibaut Courtois was far less forgiving in his assessment, lamenting Ancelotti's visitors for failing to defend two early set-pieces that brought goals for Gvardiol and Nkunku.

"It is what sometimes happens to us. We went out asleep, without intensity and you pay for it," the Belgium international added to Movistar. "The coach warned us and it still happened.

"We can't go out like that. We put in before the break. But in the second half the same, we missed a lot of passes.

"As a goalkeeper, you are noticing that we are not in the game. In many duels, we did not win. That happens in both goals, due to lack of intensity. We have to wake up.

"A bad day can happen but intensity cannot be missing. There are many on the bench and if you can't do it any more, you can't do it any more."

Madrid host Celtic on the final matchday and only have to match Leipzig's result at Shakhtar Donetsk to progress to the knockout stages as group winners.

Celtic's hopes of securing a spot in the Europa League knockout stages came to an end after a 1-1 draw with Shakhtar Donetsk at Celtic Park.

The Bhoys needed a win in their penultimate Champions League group-stage match to have a chance of continental football in the new year, and Georgios Giakoumakis put the hosts ahead nine minutes before the break, tucking in after Liel Abada's shot was blocked.

But Mykhailo Mudryk's fine form in the competition continued when he smashed in a second-half equaliser from outside the box, his fifth goal involvement in five matches (three goals, two assists).

Both sides then squandered big opportunities for a winner, with Kyogo Furuhashi firing straight at Anatolii Trubin when one-on-one and Danylo Sikan somehow missing an open goal after Mudryk's square pass.

Furuhashi's missed chance was particularly costly for Celtic as they exited Europe, unable to finish anywhere other than bottom of Group F.

Yet a Sikan winner would also have had a huge impact on Shakhtar's ambitions, as they are third and now require a win against RB Leipzig in their final match to reach the Champions League last 16.