Luciano Spalletti warned Napoli cannot think they have already reached the Champions League quarter-finals despite a dominant victory over Eintracht Frankfurt.

The Serie A leaders cruised to a 2-0 victory at Deutsche Bank Park as Victor Osimhen and Giovanni Di Lorenzo netted against Eintracht, who had Randal Kolo Muani sent off in the second half.

Napoli have never made it to the Champions League last eight but are in control of their last-16 tie ahead of the return meeting in Naples on March 15.

Spalletti refused to rest on his laurels, though, as he insisted nothing has been achieved just yet.

Asked if Napoli and Real Madrid, who smashed Liverpool 5-2 at Anfield in Tuesday's other clash, were favourites, Spalletti responded: "Will we be able to repeat it?

"We have to, let's see if we stay on track, remain in command. We cannot think we are automatically through."

Khvicha Kvaratskhelia saw Kevin Trapp save his penalty four minutes before Osimhen's first-half opener, with Napoli's poor spot-kick record continuing in the Champions League.

The Partenopei have scored just three of their six penalties taken in this year's competition, with only Monaco and Sevilla (in the 2016-17 term) missing as many in a single campaign, excluding shoot-outs, since Opta data began in the 2003-04 season.

Kvaratskhelia bounced back to tee up Di Lorenzo's calm finish, his 13th assist across all competitions this term – no Serie A player has managed more.

Spalletti referenced the resilience of Napoli being a key factor for their success.

"This thing should be highlighted here, the team didn't give up after the penalty kick, but scored immediately, insisted because we wanted to win," he added. 

"Thinking correctly, behaving like this, and wanting to win the match. We want to win them all, the matches pass so we don't come back again.

"We dreamed of this game here as children, we can't fail it. At 2-0, there was the possibility of scoring the third goal, we did some things well, others a little less, we could have tried more."

Victory marked Napoli's first away win in the Champions League knockout rounds, having lost their previous three, as they chase Serie A and European glory.

Jamie Carragher hit out at former side Liverpool after a "shambolic" Champions League showing as a rampant Real Madrid fought back to "destroy" the Reds.

Darwin Nunez and Mohamed Salah, the latter capitalising on an inexplicable Thibaut Courtois error, fired Jurgen Klopp's side into a 2-0 lead inside 15 minutes at Anfield in the first leg of their last-16 clash.

But Carlo Ancelotti's defending European champions responded in ruthless fashion, with a Vinicius Junior first-half double restoring parity before Eder Militao nodded Madrid in front in the second period.

A Karim Benzema brace secured a 5-2 lead to defend at Santiago Bernabeu on March 15, with Liverpool the first team in Champions League history to take a 2-0 lead and lose by a three-goal margin.

It marked the first time in Europe that Liverpool have conceded five goals at home as well and Carragher was left in disbelief as he launched a scathing assessment.

The former Liverpool captain said on CBS Sports: "First of all what a performance by Real Madrid to come to Anfield and do that.

"I've never seen a team come to Anfield, on a European night that I can remember, and perform and destroy Liverpool like that.

"That was shambolic from Liverpool, embarrassing, we've made excuses for them all season. 

"We've said reasons why they're not doing as well as they have done in previous seasons, but that was a disgrace in that second half."

Klopp's charges, on the back of two straight wins, had the chance to salvage the tie with the game finely poised at 2-2 at half-time.

But Liverpool, who sit eighth in the Premier League after an otherwise poor start to 2023, crumbled under the pressure – much to the disgust of Carragher.

He added: "To not even have a chance, to show any real fight after the goals go in and to lose that second half 3-0, when you're attacking The Kop and it's 2-2 in the tie, absolutely shambolic from Liverpool.

"What I'm talking about in terms of shambolic, is defensively shambolic all season. 

"It was nonsense that Liverpool were back after the last two games, they played against an Everton team who produced one of the worst performances in a derby, they did nothing.

"At Newcastle, Newcastle had 10 men and created chances, if they had 11 they would have got back in the game I'm convinced.

"That is because Liverpool right now, all season in fact, have been an absolute shambles defensively. This team had a great defensive record last season.

"The midfield doesn't have the energy any more, the attacking players don't press or have the cohesion they had before.

"This Liverpool defence, who we've been told for years have the best players in the world, can't cope. For years, they've had a front six in front of them who worked harder and smarter than any other team in football, but now they're gone they've absolutely fallen apart."

Carragher was unable to mount any kind of defence for Liverpool or Klopp, with the Reds' performance against Madrid embodying a season of underperformance and failure.

He continued: "I keep making excuses, because as Liverpool fans we adore this manager and the team as they've done so much in the last few years, but they are eighth in the Premier League and just been battered 5-2, I know by Real Madrid.

"But these two teams were in the final last year, it's not acceptable to watch this season, we keep giving reasons and excuses, but it's nowhere near good enough.

"What makes me laugh is Virgil van Dijk said I wouldn't get in their back four a few months ago – I think I'd take his place at the moment."

Virgil van Dijk and Trent Alexander-Arnold were so optimistic. After the commendable – albeit imperfect – 2-0 win over Newcastle United at the weekend, Liverpool seemed confident their luck was changing.

Liverpool had endured several previous instances this season of winning games but then struggling to build momentum.

"This feels a little bit different," Van Dijk said. Alexander-Arnold struck a similarly defiant tone.

But Jurgen Klopp's men were brought crashing back to earth in brutal fashion on Tuesday, losing 5-2 to Real Madrid at Anfield in the first leg of their Champions League last-16 tie.

Let's not forget, Madrid were arguably fortuitous 1-0 victors over Liverpool in last season's final. But here, once Carlo Ancelotti's side were on the scoreboard, this was pretty much all Madrid.

It wasn't exactly plain sailing for Madrid, but they're built differently. They're a special case.

Eduardo Camavinga said it best in an interview with the Guardian earlier this week: "People think Madrid are dead, but Madrid are never, never dead."

So when Liverpool rather astonishingly found themselves 2-0 up against the European champions inside 15 minutes, surely even the most ardent Reds fans had a twinge of trepidation deep in their minds.

Madrid have made a habit of seemingly coming back from the dead. Their route to glory last season had them resembling the undead in virtually every tie, with frankly absurd comebacks seeing them past Paris Saint-Germain, Chelsea and Manchester City.

Lucky? Perhaps, but sometimes you create your own luck, whether that's with individual quality or benefiting from individual errors.

There was a lot of both going on at Anfield on Tuesday.

Darwin Nunez's opener was a delight. Making the run in behind the Madrid defence, he anticipated Mohamed Salah's precise low pass and met it with an impudent flick of the right heel, the connection perfect as Thibaut Courtois was left helpless.

That was the sublime. Then came the ridiculous.

Courtois controlled a bouncing pass in his own area, but with Salah bearing down, the goalkeeper panicked. An accidental touch off his knee caused him to lose all control of the situation, and the Liverpool attacker duly prodded home.

The ground refused to swallow him up, forcing Courtois to cope with the very public violation of his dignity.

But nothing about the opening 15 minutes suggested Liverpool could count on a clean sheet. There were slips, spills and errors galore, the slick pitch proving rather hazardous for both sets of players.

As such, it wasn't particularly surprising when Madrid did pull one back in the 21st minute with a moment of magic of their own.

After a quick interchange with Karim Benzema, Vinicius Junior received the ball just inside the box. Seemingly surrounded, one drop of the shoulder opened up space and he somehow found the bottom-far corner.

While Liverpool chances continued to arrive, that incident felt like something of a turning point, and Alisson soon took some of the glare away from his goalkeeping counterpart.

Trying to play out from the back, his pass slammed straight against Vinicius' leg and ricocheted into the net. Klopp emitted a wry chuckle.

Suddenly it became a contest of who would respond better to such a setback. Madrid already showed their impressive hand – could Liverpool match them?

The answer was ultimately unequivocal.

Liverpool were again their own worst enemies at the start of the second half. Trent Alexander-Arnold and Joe Gomez failed to deal with Vinicius legally, the latter deemed to have fouled him on the left edge of the box.

Liverpool's defence lined up across the edge of the six-yard box. So bad was the defending here that Luka Modric didn't even try to put his delivery behind them, instead in front where Eder Militao – incredibly unmarked – was allowed to simply head home.

By now, the intensity Liverpool had shown during the first half was nowhere to be seen. At times Madrid looked like they'd struggle to give up possession even on purpose. The Reds were drained physically and emotionally – Los Blancos could smell blood.

The young Stefan Bajcetic was the next Liverpool player to commit a major error. Robbed of the ball in midfield, within seconds Madrid had the ball in the net again, the previously quiet Benzema seeing his rather tame left-footed effort deflect in off Joe Gomez.

But the fifth and final goal was all about Madrid's quality. Modric rolled back the years with a surging run before finding Vinicius, who showcased his ever-improving decision-making as he lured in the defender prior to slipping through to Benzema. He deceived three – including Alisson – with one swivel with the hips before effortlessly picking out the top-left corner.

Klopp referred to last season's Champions League final defeat to Madrid as "proper torture" – if that's an apt description, then it'll be intriguing to see how he labels this.

The Reds went from looking sensational to immensely fragile within about five minutes, and against Ancelotti's seasoned winners, that's never going to be a recipe for success.

This was the first time Liverpool have ever conceded five goals at home in Europe – it was simultaneously a harsh reality check and a grim reminder of how far they've fallen in less than a year.

Vinicius Junior and Karim Benzema heaped more Champions League pain on Liverpool as Real Madrid produced a storming fightback to secure a stunning 5-2 victory at Anfield.

Darwin Nunez's sublime flick and Mohamed Salah's strike following a Thibaut Courtois howler gave the Reds a two-goal lead only 14 minutes into a dramatic first leg of the round-of-16 tie on Tuesday.

That proved to be a false dawn as the holders stormed back in a rematch of last year's final, Vinicius pulling one back with a classy finish before a bad mistake from Alisson gifted him a second goal in an enthralling first half.

Eder Militao headed Madrid in front early in the second half before Benzema's double gave Carlo Ancelotti's ruthless side a commanding advantage to take back to the Spanish capital for the second leg on March 15.

Nunez produced a moment of magic in the fourth minute to put the hosts in front, meeting Salah's whipped ball with an audacious right-foot flick that flashed past Courtois.

Courtois endured a nightmare 10 minutes later, controlling a back past on his chest before the ball bounced off his knee to present Salah with a simple chance to double Liverpool's lead.

Madrid looked like they did not know what had hit them, but Vinicius halved the deficit in the 21st minute by showing excellent close control in the box before bending a sumptuous right-foot finish into the bottom corner.

The winger was celebrating in front of The Kop again nine minutes before the break after Alisson's terrible attempted pass struck his Brazil team-mate and looped into the net.

Madrid lost David Alaba to injury during a pulsating first half which they would have ended with a lead had Andy Robertson not shown great awareness to deny Rodrygo a tap-in.

Los Blancos were in front two minutes into the second half, though, when an unmarked Militao capitalised on terrible defending to head in the influential Luka Modric's free-kick.

An evening that had started well then took another turn for the worse for Liverpool, with Benzema's shot striking Joe Gomez and giving a wrong-footed Alisson no chance.

Liverpool were opened up again after 67 minutes, Modric and Vinicius combining before Benzema sat Alisson down and demonstrated great composure to finish with his left foot.

Napoli took a significant step towards their first Champions League quarter-final after a 2-0 victory over 10-man Eintracht Frankfurt on Tuesday.

Victor Osimhen's 40th-minute opener at Deutsche Bank Park set Napoli on their way in the first leg of their last-16 clash after Kevin Trapp saved a Khvicha Kvaratskhelia penalty.

Randal Kolo Muani's red card after 58 minutes only served to further Napoli's cause before Giovanni Di Lorenzo netted to secure a comfortable lead in the tie.

Eintracht will have the chance to fight back in Naples on March 15, though it appears little can stop Luciano Spalletti's Serie A leaders at present.

Kolo Muani blasted an early warning shot wide after a smart flick past Amir Rrahmani, but Napoli soon began to dominate.

Their pressure told as Aurelio Buta needlessly felled Osimhen inside the area after Hirving Lozano struck the right post, only for Trapp to dive to his right to save Kvaratskhelia's poor penalty.

Napoli did reap their rewards four minutes later, though, as Osimhen turned in Lozano's right-wing cross, with the same combination then denied a swift second by an offside flag.

Trapp parried away a swerving Lozano attempt after the interval before Kvaratskhelia wasted a glorious chance with a chip straight at the onrushing Eintracht goalkeeper, but matters went from bad to worse for Eintracht soon enough.

Kolo Muani was shown a straight red for a lunge on Andre-Frank Zambo Anguissa, and Napoli capitalised as a smart Kvaratskhelia backheel found Di Lorenzo, who curled low into the bottom-left corner to secure a two-goal cushion.

What does it mean? Business as usual for in-form Napoli

Eintracht had lost only two of 19 matches in Europe under Oliver Glasner – and just one in nine on home soil – but Napoli present an entirely different challenge this season.

Although Spalletti's in-form side, who have won 20 of 23 Serie A games this term, were slow to get going, Eintracht had no answer once they found their feet.

Napoli have never progressed past this round in the Champions League, but it will take something special to stop the rampant Partenopei this time.

Unstoppable Osimhen

Osimhen's remarkable form has led to speculation around a move to Manchester United or Chelsea, but his focus for now is on Napoli's dual bid for Serie A and Champions League glory.

The Nigeria international certainly did not appear distracted as he scored in a sixth successive match – his best streak for Napoli. 

Error compounds Eintracht misery

Kolo Muani embodied Eintracht's early promise, with his nimble footwork and pace causing repeated problems down the right flank.

But hopes of a positive outcome in this first leg – and perhaps in the tie, too – were erased after a reckless tackle was rightly punished.

What's next?

Napoli return to action in Serie A with a Saturday trip to Empoli, while Eintracht travel to RB Leipzig in the Bundesliga on the same day.

Pep Guardiola's mindset is just to enjoy leading Manchester City in the Champions League rather than worrying about talk of a "disaster" if they still cannot win Europe's elite club competition.

Guardiola won the Champions League twice while Barcelona coach but has failed to add to that haul in otherwise successful stints in charge of Bayern Munich and City.

Perennial Premier League champions City have been repeatedly frustrated in Europe, consigned to upset losses to Monaco, Liverpool, Tottenham and Lyon in the knockout stages in Guardiola's first four seasons.

City then reached the final in 2020-21, only to again come up short against Chelsea.

Last year, there was a painful semi-final reverse at the hands of eventual champions Real Madrid, increasing external pressure on one of the greatest coaches of the modern game.

But ahead of entering the knockout rounds again against RB Leipzig on Wednesday, Guardiola revealed he has learned to look at life very differently – influenced by the negative outlook of others.

"From the first season, I get this," he said initially. "I arrive here, and people say, 'you arrive here to win the Champions League'."

Guardiola then added: "I would say if my career finished tomorrow, if I could not be manager literally tomorrow, I would be more than blessed with what I've done at Barcelona, Bayern Munich and here in Europe and in other competitions.

"I could never expect to have the career I had in this short time. Not just the success we had all together over this period of 13, 14 years, but for the fact the way we played, this way I love it. I couldn't ask more.

"We want to do our best. What's going to happen is going to happen. In the end, destiny is already written. We'll do our best, as we have done. We have been close sometimes, sometimes not, sometimes closer.

"This is my feeling. I lived that position. I had the feeling of what we have done, all of us for many years, whatever happened, it is going to fail.

"Whatever I do personally in the future, whatever I have done in the past, I'm going to fail. Nothing will be enough.

"When I learned that, I just have fun, enjoy being here in this press conference. After, a good dinner with good wine, watch Liverpool-Madrid, a little bit Napoli, always a pleasure, prepare well the game.

"Leave it for the players: let's go, guys, try to do it again."

Guardiola said he had started to feel like this "a long time ago" but "mainly at City".

He continued: "Everyone put the perspective that everything is a disaster if you don't win some prizes. But I don't know if everyone put this perspective on themselves.

"I don't want to put pressure on myself. I'm blessed to be here.

"I never thought when I arrived, we have to win every year the Premier League, or every year we have to win three or four Champions Leagues. Except Real Madrid, the rest cannot do it.

"We just try to do what we have done. The last two seasons we have been really close and played really good games. We'll try to do it again."

Kevin De Bruyne and Aymeric Laporte will miss Manchester City's away game against RB Leipzig with illness, Pep Guardiola revealed.

De Bruyne and Laporte were surprise absences from the City squad for the first leg of their Champions League last-16 tie.

But Guardiola was able to confirm the nature of their problems after landing in Germany.

The City manager was unsure if either player – both of whom started against Nottingham Forest on Saturday – would return for this weekend's game at Bournemouth, having come down with illness in recent days.

Those absences will leave Guardiola with decisions to make around his team selection, although he had already been provoking some curiosity by naming Bernardo Silva, a midfielder, at left-back.

Fabian Delph and Oleksandr Zinchenko fulfilled that role previously, but Silva struggled against Arsenal's Bukayo Saka and then appeared to be at fault for Forest's equaliser on Saturday.

Guardiola said he was "not so stupid to think Bernardo is a full-back" as he explained his thought-process.

"People say we conceded the goal on the left side because Bernardo's playing there, but people don't realise – the view is like he's a left-back who has to defend in that position," he said.

"Bernardo helped us to do what we had done against Nottingham Forest. Without Bernardo, it was not possible to concede [only] one counter-attack and one or two actions at the end and [have] the amount of control of the game."

Kevin De Bruyne and Aymeric Laporte have been left out of Manchester City's squad to play RB Leipzig in the Champions League on Wednesday.

John Stones is also absent from the group, although he has been missing since January with a hamstring injury.

There was no immediate explanation for De Bruyne and Laporte not travelling to Germany, with Pep Guardiola due to meet the media later on Tuesday.

Both players started Saturday's 1-1 draw at Nottingham Forest. De Bruyne was substituted in the 88th minute, while Laporte completed the match.

Meanwhile, Leipzig were hoping to have Christopher Nkunku available after he returned to action for the first time since November.

Having played at Wolfsburg at the weekend, Nkunku could not complete Leipzig's full training session on Tuesday, the club said, due to a muscle issue.

Simone Inzaghi could not assure Romelu Lukaku he would start again against Porto despite ending his goal drought on Saturday.

Lukaku has scored only three times since returning to Inter at the start of this season.

It has been a difficult campaign for the Belgium forward, who also failed to net at the World Cup in Qatar.

But a penalty against Udinese on Saturday gave Lukaku his first Serie A goal since August ahead of Wednesday's Champions League last-16 first leg against Porto.

That does not mean Lukaku is certain to start, however, as coach Inzaghi said in his news conference there were "doubts" about his line-up.

Edin Dzeko would be the obvious alternative to Lukaku, having netted 11 in all competitions this season, although the pair started together against Udinese.

Asked specifically about Lukaku and midfielder Marcelo Brozovic, Inzaghi said: "Lukaku has been working for longer and is improving. He is putting a great deal of effort into it.

"As for both, tomorrow we will try to make the best choices for Inter.

"Those who do not start will still be useful in the game. In games like these, the final minutes are those in which decisive actions can occur and spaces are freed up to exploit."

Inter have not been past the last 16 of the Champions League since the 2010-11 season, when they were playing as defending champions.

But having emerged from a difficult group that also included Barcelona and Bayern Munich, confidence is high.

"We face this tie with great confidence," Inzaghi said. "We reached it with an incredible path – on paper, Barcelona and Bayern Munich were teams that everyone wanted to avoid.

"You can see what Barca are doing in La Liga, and we know what Bayern are."

Napoli should be considered favourites to win the Champions League after dominating Serie A this season, according to Milan great Ruud Gullit.

Luciano Spalletti's dynamic Napoli side have been one of the stories of the European season, boasting a 15-point lead at the Serie A summit after losing just once in their first 23 league games. 

The Partenopei have also excelled in the Champions League, top-scoring in the group stage with 20 goals to finish above Liverpool and tee up a last-16 tie with Eintracht Frankfurt.

Speaking to La Gazzetta dello Sport ahead of Napoli's trip to Germany for the first leg of that tie, Gullit suggested Europe's elite clubs may struggle to match Spalletti's men. 

"In a television broadcast I said that they are the favourites to win the Champions League. I haven't changed my mind," the former Netherlands international said of Napoli.

"They play a style of football that we all like to see; fast, rapid and vertical. 

"The English clubs are strong, the same for Bayern Munich, and Real Madrid are capable of crazy feats, but this Napoli team are totally different." 

Napoli's last Scudetto came in the 1989-90 season, when Diego Maradona inspired them to edge a hard-fought title race against a legendary Milan side featuring Gullit.

Asked about the differences between Napoli teams past and present, Gullit said: "That team depended on Diego. This is a complete team, which expresses total football. They can win the Scudetto and go far in Europe."

Gullit's former employers Milan are also looking to mount a challenge in Europe, having beaten Tottenham 1-0 in the first leg of their own round-of-16 tie.

Having recently endured a seven-game winless run, Milan sit fourth in Serie A and trail Napoli by 18 points, but Gullit refuses to write the Rossoneri off. 

"They are fighting and suffering," he said of Stefano Pioli's men. "Up to now, everything hasn't been as easy as it was last year. 

"In this first part of the season things have been more difficult than everyone expected, but in football you never know. In the Champions League they won the first leg of the round of 16 against Tottenham. Let's see how it ends."

Reported Manchester United and Chelsea target Victor Osimhen has refused to rule out a move in the next transfer window, though the Napoli star is focused on delivering silverware before then.

Osimhen has hit 18 goals to help Napoli build a 15-point advantage at the Serie A summit – only Manchester City's Erling Haaland (26) has outscored him in Europe's top five leagues this term.

The Nigeria international scored in a seventh consecutive league game in Napoli's 3-0 thrashing of Sassuolo last week, and his electrifying form has reportedly attracted Premier League suitors. 

United and Chelsea have both been credited with an interest in Osimhen, who Napoli president Aurelio De Laurentiis insists is not for sale.

While helping the Partenopei clinch the Scudetto for the first time since the Diego Maradona era is his current focus, the striker has left the door ajar for a move at the end of the campaign.

"When you are doing so well, top clubs around the world are watching, mostly in the top five leagues," Osimhen told ESPN.

"To be able to be attract interest from these top clubs shows that I am doing great, and it gives me the motivation to do even more for myself and my team.

"But I am focused on Napoli right now and they have the final say. I just want to help my team to win matches and win trophies.

"At the end of the season, we will see what is going to happen, but that is not up to me. It is for the club to decide."

Napoli travel to Eintracht Frankfurt for the first leg of their Champions League last-16 tie on Tuesday, having top-scored in the competition's group stage with 20 goals – though only one of those came from Osimhen.

Liverpool welcome Real Madrid to Anfield on Tuesday in the Champions League round of 16, and the latest meeting of Jurgen Klopp and Carlo Ancelotti.

Their respective histories could have been so different.

After Everton and Liverpool had played out a 1-1 draw at Goodison Park in October 2015, in the Sky Sports studio, Thierry Henry reached across and placed his hand on a bewildered Jamie Carragher's knee as the news was announced that Brendan Rodgers had been dismissed as Reds manager.

Within minutes, the favourites for the role were being discussed, with frontrunner Klopp ultimately being the man to come in and take the club back to the summit of English and European football.

The second favourite had been Ancelotti, out of work at the time following his exit from his first spell at Madrid, and Carragher argued that while the Italian had the more impressive CV, Klopp was the more suitable choice for the Anfield hotseat after his success at Borussia Dortmund.

"I think with either of those coming to Liverpool, the supporters would be ecstatic," he said at the time. "If it was me, I would go for Klopp ahead of Ancelotti. I think he's got more to prove. Ancelotti is a great manager of course, but he's gone to clubs where you would expect to win trophies.

"It's a difficult job now at Liverpool getting them back into the top four. Forget talking about the title. And I think it needs someone with that energy and drive to get Liverpool back to where it wants to be and I think Jurgen Klopp's that man."

Of course, Carragher proved to be right about Klopp.

It will never be known what would have happened had Ancelotti been hired instead, but he has gone on to enjoy success at other clubs since, with spells at Bayern Munich, Napoli and Everton before heading back to the Santiago Bernabeu in December 2021.

The two have faced off numerous times in opposing dugouts, with the upcoming two-legged Champions League tie set to be their 12th and 13th meetings.

It is interesting how frequently Klopp and Ancelotti have come up against one another, especially considering the Italian's 18-month spell at Everton was the only time they have managed in the same league.

They clashed on four occasions in Merseyside derbies – coincidentally after that had been the fixture that led to their names being linked with the Liverpool job back in 2015 – with two draws at Goodison Park in the Premier League and a 1-0 Liverpool win in an FA Cup third round game at Anfield.

The most notable encounter also came at Anfield in February 2021, with no fans in due to COVID-19 restrictions, where Ancelotti masterminded Everton's first win at the home of their neighbours since the turn of the century.

Their other seven meetings have come in the Champions League, Klopp coming up against Ancelotti for the first time during his penultimate season at Borussia Dortmund as they took on Madrid in the last eight, losing 3-0 in the Spanish capital before a spirited but unsuccessful 2-0 reverse back in Dortmund.

Two goals from Marco Reus in the first half had given the German side hope of a comeback, but Ancelotti's men put up the defences and managed to see the game out, a tactic that the Los Blancos head coach has used to good effect against Klopp on numerous occasions since.

He also frustrated Klopp in their first meeting as Liverpool and Napoli bosses respectively, with the Serie A side winning 1-0 at home in the 2018-19 group stage, restricting the Reds to just four shots – none on which were on target – as Lorenzo Insigne struck a late winner.

A Mohamed Salah goal in the reverse fixture was enough to send Liverpool through to the knockout stage with a 1-0 win at Anfield at Napoli's expense, with the Reds going on to lift the trophy in Madrid that season.

The two teams were drawn together again in the group stage the following year, with Napoli again defeating Liverpool in Naples, 2-0 this time, while they played out a 1-1 draw back on Merseyside.

Klopp and Ancelotti would not meet again in the Champions League until after their brief Merseyside derby rivalry, somewhat appropriately in the final as Liverpool faced Madrid in Paris last season.

While the game was heavily distracted by the chaos outside prior to kick-off that an independent investigation has since claimed was the fault of UEFA and the French authorities, on the pitch it had a feel of Klopp's previous struggles with Ancelotti.

Liverpool dominated large parts of the contest, but Madrid were largely able to contain them, though goalkeeper Thibaut Courtois still had to put in an outstanding performance to keep a clean sheet.

Ancelotti suggested after the 1-0 win thanks to a Vinicius Junior goal that Klopp's team were "more decipherable" than others he had faced, but ahead of their next clash, the German coach lavished praise on his opposite number.

"Carlo is the most relaxed manager I ever met in my life," Klopp said at his pre-match press conference. "One of the best people you can meet, fantastic person, a humble person, super smart and nice, and obviously his man management is at a completely different level to all of us, and I respect that a lot and admire it a lot."

Ancelotti reciprocated at his press conference, saying: "I have a good relationship with Klopp. We stayed for a year and a half in Liverpool during the pandemic, and we used to text each other and exchange gifts. He's a really lovely person."

There is clear mutual respect there, strengthened by the duo's personal achievements as well as how difficult they both find games against one another.

Klopp's teams have only managed to find the net seven times against Ancelotti's in 11 games, despite having 153 shots, suggesting the former Milan, Chelsea and Paris Saint-Germain boss knows how to restrict them to low-quality chances.

Ancelotti has relied on his team's defensive solidity more often than not, and boasts the superior record with five wins to three defeats and three draws, but he has never been able to beat a Klopp team in an away game when fans have been in attendance, with a noisy Anfield on Tuesday a near certainty.

He surely takes slightly more pleasure in besting Liverpool than he does most other foes following one of his most painful defeats as a coach when his Milan side was beaten on penalties in the iconic 2005 Champions League final in Istanbul, despite leading 3-0 at half-time.

This season's final will also be in the Turkish capital, but at least one of Liverpool or Ancelotti will not be there this time.

Klopp v Ancelotti. Germany v Italy. Beard v eyebrow. It is one of the great modern coaching rivalries, and round 12 should be another fascinating contest.

In a rematch of the 2022 Champions League final Real Madrid will travel to Anfield on Tuesday on a mission to inflict more pain on Liverpool in the round of 16.

Madrid got their hands on the famous trophy in Paris last May, but while the Reds have struggled in the Premier League this campaign, their European form would suggest they should provide a tough test for a side who have had their number in recent years.

Meanwhile, reigning Europa League champions Eintracht Frankfurt will look to continue their sparkling European form when runaway Serie A leaders Napoli roll into town.

Napoli have taken on all comers this season, proving to be a force in Europe while they have taken Serie A by storm.

Courtesy of Stats Perform, here are some of the key stats and facts to be aware of ahead of the ties.

Liverpool v Real Madrid

Memories of last season's Champions League final will be fresh in the minds of these two sides as Liverpool try to reverse the recent trend of Madrid dominance.

The Spanish giants lifted the top prize in European club football for a 14th time after defeating Liverpool 1-0, leaving the English side winless in their past six meetings between the clubs.

That is the longest winless streak Liverpool have suffered against any team in their Champions League history, with five losses and one draw dating back to 2009.

However, England has not been a happy hunting ground for Madrid in recent years, with only one victory – against Chelsea in 2022 – from their past seven away fixtures in the country (D2 L4).

Also in the hosts' favour is their terrific European form this season, having rattled off five consecutive wins in the competition since losing their opener against Napoli.

A key for the Reds will be figuring out how to stop Vinicius Junior, who has directly contributed to seven goals – scoring five and producing two assists – in his past eight Champions League fixtures.

Liverpool forward Mohamed Salah could join Chelsea legend Didier Drogba as Africa's all-time leading scorer in the competition with one more goal, which would be his 44th.

Eintracht Frankfurt v Napoli

Napoli will be dreaming of their first Champions League and Serie A double as they hit the road for their first leg against Frankfurt.

They will face a German side who have excelled in European competition under head coach Oliver Glasner, with only two losses from 19 matches (W10 D7), including a triumph in last season's Europa League final against Rangers.

Frankfurt have won their past four meetings with Italian sides since a loss to Palermo back in 2006, while Napoli have just two wins from their 12 away dates in Germany (D5 L5).

But Napoli have been a different beast this campaign, leading all teams with 20 group stage goals. They are averaging 3.3 goals per game in the competition under Luciano Spalletti.

Breakout star Khvicha Kvaratskhelia is at the centre of Napoli's success, joining Dries Mertens (2017-18 season) as the only players in the history of the club to record multiple games with a goal and an assist in the same Champions League campaign. He has the potential to write his own history, as no Napoli player has done it three times.

Meanwhile, Frankfurt have a pair of in-form goalscorers. Daichi Kamada has scored in each of his side's past three Champions League matches this season, while Randal Kolo Muani has found the back of the net in their past two.

Luciano Spalletti has backed star Napoli pair Victor Osimhen and Khvicha Kvaratskhelia to rise to the occasion as they prepare to face Eintracht Frankfurt in the Champions League last 16.

Osimhen and Kvaratskhelia have been two standout performers for Napoli this season, who boast a 15-point lead in Serie A and coasted through their Champions League group earlier this season.

Ahead of their first leg in Germany against the reigning Europa League holders, Spalletti heaped praise on both, as well as the club's decision-makers who brought them to Naples.

"From the point of view of maturity, we can cite Osimhen's reaction to Sassuolo [on Friday] as an example [when he asked to come off after feeling a potential injury]," he told reporters. "As soon as he realised he had a little problem he evaluated correctly, asking for a substitution.

"This is the player who knows how to evaluate things very well, these two types [Osimhen and Kvaratskhelia] they are two of those who truly have the flair, the imagination, the quality to send a message to world football. At the same time, they are two very young boys.

"[Sporting director, Cristiano] Giuntoli and [chairman, Aurelio] De Laurentiis were good at choosing them from a very large group of players, this youth still needs to be shaped, matured.

"Tomorrow night will be an event to be attacked. In my opinion they will be able to interpret it. It is not allowed to be afraid. We will see football that only those at this level can make."

The former Roma and Inter head coach also leaned into a Christmas analogy put to him by a reporter, comparing the Champions League knockout stage to Christmas morning.

"I have to give the reindeer some milk, because it's the night before, it's a party for me," he replied. "We'll see if we can unwrap the presents or not."

Spalletti will go up against opposite number Oliver Glasner, who has impressed at Eintracht since taking over in 2021.

"I know him well because I had already met him when I was coach of Zenit, there is mutual respect as regards the work of the other, for my part," the Italian said. 

"I have a number of people who Napoli makes available to me and who go to see the work of the teams that manage to play good football. Since he won the Europa League we too have gone to see what Glasner is doing.

"He is modern, he knows how to make his team play very short, he knows very well how to press high and bring the team block low and start again in space. He has players who know how to use this space very well.

"We congratulate him on the football he has played, he is doing it even in the league. Precisely for this reason it will be delicate and difficult."

Karim Benzema will start the first leg of Real Madrid's Champions League tie with Liverpool, says Carlo Ancelotti, who is backing Vinicius Junior to shine against the Reds once again.

Madrid were without Benzema for Saturday's 2-0 win at Osasuna, with Ancelotti intent on managing the striker's minutes after he endured an injury-hit few months.  

Ancelotti said the 2022 Ballon d'Or winner would not have faced Liverpool had the first leg of the last-16 tie taken place on Saturday, raising fears he could miss out on Tuesday.

However, Benzema – who top-scored with 15 goals in 12 Champions League appearances last season – has been passed fit to feature from the off on Merseyside.

Asked about Benzema's availability at Monday's pre-match press conference, Ancelotti said: "I see Benzema looking well, tomorrow he will start."

Benzema is looking to end a five-game goal drought in the Champions League, having failed to net in 324 minutes in the competition since his decisive penalty in last May's semi-final second leg against Manchester City.

While Benzema will start, Madrid will be without midfielders Toni Kroos and Aurelien Tchouameni at Anfield, but Ancelotti is backing others – including Luka Modric – to step up.

"I'd like to have them," he said of the midfield duo. "It's a forced transition that we didn't want. It doesn't worry me because the feeling we have without them is good. 

"Those who have replaced Toni and Tchouameni have done well and we have confidence in the whole squad.

"Modric didn't have a good time in January but now he's back to his best level and he's going to keep growing. His condition is good and he still wants to play for Madrid."

Madrid's last meeting with Liverpool was a memorable one for followers of Los Blancos, as Vinicius' goal handed them victory in last season's Champions League final in Paris.

The Brazilian has enjoyed another outstanding campaign for Madrid, though it has been marred by several incidents where he has faced racist abuse from the stands at LaLiga games.

Asked if Vinicius was looking forward to a fixture outside of Spain, Ancelotti said: "He likes to play anywhere. Vini is handling it well and it doesn't affect his performance on the pitch.

"The issue of racism is very serious and complicated, there is no law that changes a person's head, that is done by culture and common sense.

"I don't blame Spain for this, things like this happen in all countries. The most important thing is respect for people.

"Also, this is a very important match. Right now it's a pleasure to watch Vini, not just for Madrid but for all of football. 

"Everyone likes to see his quality and his talent, like with Pedri, Gavi, [Kylian] Mbappe and [Erling] Haaland... It's a pleasure for football to be able to enjoy this quality."