Real Madrid and Liverpool will contest a repeat of last season's Champions League final during the round of 16 following Monday's draw.

Madrid reached the knockout stages as Group F winners, an outcome they will have been hoping would secure them a favourable tie.

But by being paired with Liverpool, Carlo Ancelotti's men were given arguably the hardest draw possible in what will be a repeat of the 2021-22 and 2017-18 finals.

There will also be a replay of the 2019-20 showpiece between Bayern Munich and Paris Saint-Germain.

Die Roten prevented PSG from winning their first continental crown that year, with revenge on the cards for the Parisians early next year.

Chelsea, winners most recently in 2021, will go up against the youthful Borussia Dortmund, while Manchester City – beaten finalists last year – are also due to tussle with Bundesliga opposition in RB Leipzig.

Antonio Conte faces a return to his homeland and San Siro as Tottenham prepare to duel with Italian champions Milan, while Serie A leaders Napoli – who won their group ahead of Liverpool – will fancy their chances against Europa League holders Eintracht Frankfurt.

Last-16 draw in full:

RB Leipzig v Manchester City
Club Brugge v Benfica
Liverpool v Real Madrid
Milan v Tottenham
Eintracht Frankfurt v Napoli
Borussia Dortmund v Chelsea
Inter v Porto
Paris Saint-Germain v Bayern Munich

Real Madrid and Liverpool will contest a repeat of last season's Champions League final during the round of 16 following Monday's draw.

Madrid reached the knockout stages as Group F winners, an outcome they will have been hoping would secure them a favourable tie.

But by being paired with Liverpool, Carlo Ancelotti's men were given arguably the hardest draw possible in what will be a repeat of the 2021-22 and 2017-18 finals.

Milan forward Rafael Leao continues to be linked with a host of top European clubs who are plotting January moves.

Leao won last season's Serie A Footballer of the Year and has maintained his fine form this term.

The 23-year-old forward is contracted with Milan until mid-2024, prompting interest to prise him away from the Rossoneri.

TOP STORY – MILAN PREPARING FOR BUMPER JANUARY BIDS FOR RAFAEL LEAO

Milan are preparing for January bids from Chelsea and Manchester City of approximately £105 million for Rafael Leao, reports Tuttomercato.

Manchester United and Paris Saint-Germain have also shown an interest in the Portuguese attacker.

Milan are still working on a new deal with Leao before he departs for the World Cup, hoping to tie him down on a long-term contract.

ROUND-UP

– Manchester United boss Erik ten Hag is considering trying to lure Dusan Vlahovic to Old Trafford as he prepares for life without Cristiano Ronaldo, reports The Sun on Sunday. Juventus forward Vlahovic moved to the Bianconeri from Fiorentina in January for £62million.

– Arsenal manager Mikel Arteta has told the club to sign Leicester City midfielder Youri Tielemans in the January transfer window, claims The Sun. Tielemans is valued at £40m and is out of contract at the end of this season.

– The Mirror reports Arsenal are also interested in a January move for Vitoria Guimaraes midfielder Ibrahima Bamba, having sent scouts to watch him.

– Calciomercato claims Tottenham are looking into a swap deal involving Emerson Royal in order to bring Dutch defender Denzel Dumfries to the club from Inter.

– Serie A leaders Napoli are preparing an offer for Barcelona's Jordi Alba, who is looking for first-team football, according to El Nacional.

Stefano Pioli believes the character of his Milan side is "second to none" after the reigning Serie A champions secured a late win against Spezia on Saturday.

Olivier Giroud came off the bench at San Siro to score an 89th-minute winner in the 2-1 victory, though was then sent off for a second booking after removing his shirt while celebrating.

Pioli was full of praise for the mental strength of his team after the win, which took Milan up to second and back to within six points of league leaders Napoli after the latter beat Atalanta.

"Our mentality is to believe in what we do," he told Sky. "As far as character is concerned, we are second to none."

Theo Hernandez put Milan in front with a first-half volley from close range, only for Daniel Maldini - son of Milan legend and technical director Paolo - to equalise against his parent club with Spezia's first away goal of the season.

Maldini's goal came 5,333 days after his father's last one at San Siro in March 2008.

Pioli did not seem to mind Maldini scoring, particularly because his team eventually secured the win, and declared that his father was able to experience the best of both worlds, with his son scoring and his team winning.

"Daniel Maldini's goal? It was the perfect evening for Paolo," the Rossoneri head coach joked.

"The match was difficult, we made it complicated... I liked the first half, [but] we have to work to close the game early."

On Giroud's red, with the French striker later claiming he had forgotten he was on a yellow card, Pioli said: "He is a very strong guy, and I am very happy with his performances.

"Tonight, he was naive."

Olivier Giroud was "angry" with himself for forgetting he had already been booked when he whipped off his shirt to celebrate scoring Milan's late winner against Spezia.

Giroud came off the bench to snatch a 2-1 victory for the Rossoneri with an 89th-minute volley after being picked out by a superb Sandro Tonali pass.

The France striker was then given his marching orders, having been shown a yellow card six minutes before scoring his decisive goal.

Giroud has been in the thick of the action this week, scoring two goals and providing as many assists in a 4-0 thrashing of Salzburg that put Stefano Pioli's side in the Champions League round of 16.

The 36-year-old was frustrated that his earlier caution had slipped his mind after his clinical finish in the closing stages at San Siro.

"It was certainly a very nice goal, which came thanks to Tonali's assist," he told Sky Sport. "We wanted to win this match, the important thing is to have three points more in the standings but I'm angry because I forgot about the first yellow card."

Asked if he was not thinking clearly due to the ecstasy of scoring the winner, he replied: "Yes, football is like that. The adrenaline and the happiness of having given victory to the team after a difficult match has affected me.

"In my head I am still a child, but I have great faith in the team and also on Tuesday [against Cremonese] we will fight to win the three points."

Theo Hernandez put Milan in front with a first-half volley from close range, but Daniel Maldini equalised against his parent club with Spezia's first away goal of the season.

Tonali had a goal ruled out at 1-1 for a foul on M'Bala Nzola by Fikayo Tomori following a VAR check, but Giroud moved them six points behind Napoli in second place after the leaders beat Atalanta 2-1 earlier on Saturday.

Olivier Giroud scored a late winner and was sent off for his celebration as Milan beat Spezia 2-1 to go second in Serie A.

Theo Hernandez put the Rossoneri on course for back-to-back wins after they hammered Salzburg to qualify for the Champions League round of 16 in midweek.

Daniel Maldini, son of Milan legend Paolo, then stunned his parent club by scoring Spezia's first away goal of the season to equalise in the second half.

There was late drama at San Siro, though, as Giroud came off the bench to volley an 89th-minute winner before being shown a second yellow card for whipping off his shirt.

Barcelona have reportedly reignited their chase of Manchester City midfielder Bernardo Silva, and are said to be confident in their ability to get the deal done in January.

Silva, 28, has won four league titles with City since arriving at the club in 2017, and is enjoying another strong season after setting a new career-high with eight Premier League goals in the 2021-22 campaign.

The Portuguese international with 72 senior caps has two goals and five assists in his 12 league appearances this season, and has appeared in all six of City's Champions League group stage fixtures.

Barcelona have been linked with Silva for months, but after recent reports claimed they had moved on, a recent development has positively impacted the Spanish giants' financial situation and put the City star back on their radar.

TOP STORY – BARCELONA REVISIT CITY'S SILVA AFTER PIQUE RETIREMENT

According to Sport, the retirement of Gerard Pique has resulted in significantly improved financial flexibility for Barcelona, allowing them to revisit their long-standing interest in Silva.

The report claims City may be hesitant to part ways with a key contributor in the midst of a title chase, but that Silva had previously asked to leave the club before the failed sale of Frenkie de Jong muddied the waters.

Meanwhile, Mundo Deportivo adds Barcelona will look at 31-year-old Athletic Bilbao centre-back Inigo Martinez as their top choice to fill the defensive void left by Pique's departure.

ROUND-UP

– Calciomercato is reporting Chelsea are preparing to terminate the loan of Denis Zakaria, claiming they can not offer him regular starts and have no interest in activating the €28million buy clause in the deal.

– According to ESPN, Liverpool are the favourites ahead of Chelsea, Real Madrid, Manchester United and City to land Borussia Dortmund phenom Jude Bellingham.

– The Leicester Mercury is reporting Leicester City will not allow Youri Tielemans to leave during the January transfer window, despite his contract expiring at the end of the season.

– Milan are keeping a close eye on 22-year-old Spezia centre-back Jakub Kiwior, with Gazzetta dello Sport reporting they could make a move in January.

– According to La Razon, Aston Villa manager Unai Emery is interested in 25-year-old centre-back Pau Torres, who he coached at Villarreal.

LaLiga has warned a fresh attempt to launch a European Super League will be offering only a rehashed version of the competition that launched and collapsed within days last year, leaving clubs humiliated.

The Spanish league is determined to fend off a new proposition for an elite league, and has warned it would "destroy" the existing structure of the domestic game.

In a statement, LaLiga pointed to a previous proposal from 2019, as well as the calamitous launching of the Super League last year that saw 12 teams agree to take part, before almost all pulled out in a hurry after a furious backlash from fans, politicians and football governing bodies.

It was revealed in October 2022 that A22 Sports Management – a company representing the Super League clubs – is planning to revive the proposals. Bernd Reichart, a media executive, has been appointed to head up the plans.

LaLiga said on Twitter on Friday: "The promoters of the Super League are now preparing a model similar to the one put forward in 2019, which is still closed or mostly closed, which will destroy the national leagues and which has already been rejected by clubs and leagues in Europe."

Spanish giants Barcelona are among the teams still keen on the idea of a new competition, with club president Joan Laporta last month saying it would be "more even" than the current system, claiming UEFA is not satisfactorily enforcing the ethos of financial fair play.

LaLiga published a video expressing its opposition to the Super League, in which it stated that "the whole of European football took a stand against its closed, selfish and elitist model".

"Now the promoters of the Super League are trying to conceal its format, claiming that they still don't have a fixed model although it will be an inclusive and open," LaLiga added.

"We know that this is false, and that they want to present a semi-closed format similar to 2019 which has already been rejected by the clubs and European leagues.

"This model is based on promotion and relegation between European divisions where the national leagues do not provide direct access to the top tier. On the contrary, they perpetuate the participation of a privileged few, even if they perform poorly in their domestic leagues.

"To be clear: anything less than any club earning its place in Europe's top flight through success in the domestic leagues will remain a closed or semi-closed model.

"We have also heard that the Super League wants to claim to be the saviour of football, saying that the current system no longer appeals to young people. Fake news. As an example, data shows that LaLiga's audience in Spain among those under the age of 24 has increased by more than 22 per cent in the last four seasons."

LaLiga also said research showed football's global fan base had risen by 3.4 per cent in the 16-29 age bracket, while stating TikTok metrics revealed 60 per cent of its mainly young audience consumes football content.

The statement from LaLiga said the Super League's promise of "a more exciting competition" would in reality mean "a constant stream of the same type of clashes, turning the extraordinary into the ordinary".

It warned such a competition "would destroy the ability to turn dreams into reality", denying smaller clubs than the cherry-picked elite the long-established pathway to competition at the highest level.

LaLiga, whose president Javier Tebas has been a vocal opponent of the proposed new competition, added: "The promoters of the Super League must respect the will of European fans and citizens, where the Council of Europe has already taken a position against the Super League and the European Parliament has defended an open, democratic model based on meritocracy."

Atletico Madrid were eliminated from Europe in midweek after a 2-1 loss at Porto and are looking to bolster their squad.

One player who could be sold is Joao Felix, who Atleti signed for €126million from Benfica on a seven-year deal in 2019.

The Portuguese forward has underwhelmed this season, with only two goals, and has been unsettled at times.

TOP STORY – ATLETICO WILLING TO LISTEN TO JOAO FELIX OFFERS

Cadena SER claims Atletico Madrid have put Joao Felix on the market and are open to offers for him.

Bayern Munich were rumoured to have made a €100m off-season move for Felix, while Manchester United reportedly had a €130m bid turned down in August.

Fichajes reported last month that the 22-year-old had handed in a transfer request, while Paris Saint-Germain and Barcelona have been linked with him recently.

ROUND-UP

– Real Madrid are getting proactive in the pursuit of Palmeiras' 16-year-old talent Endrick, sending officials to Brazil to commence talks over a deal, claims Marca. Endrick cannot officially join Madrid until he is 18-years-old but Los Blancos are eager to get an agreement in place.

– West Ham, Leicester City, Southampton and Brentford are all monitoring Lyon's Brazilian winger Tete, according to The Sun.

– Diario Sport reports Barcelona want to sign Athletic Bilbao centre-back Inigo Martinez as a replacement for the retiring Gerard Pique.

– Leicester are weighing up their options for a Youri Tielemans replacement, keeping tabs on Lorient midfielder Enzo Le Fee, reports 90min.

– La Gazzetta dello Sport reports veteran French forward Olivier Giroud will be rewarded with a new Milan contract after the World Cup. The new deal will run until 2024.

Erling Haaland's Manchester City progress will be down to Pep Guardiola's ego, says Zlatan Ibrahimovic, while the striker also thinks Kylian Mbappe made a mistake staying with Paris Saint-Germain.

Norway international Haaland arrived at the Etihad Stadium during the last transfer window from Borussia Dortmund and has thus far lived up to the hype that surrounded his signing.

With 22 goals in a combined 15 games between the Premier League and Champions League already, the sky appears to be the limit for the forward this season.

But veteran Milan attacker Ibrahimovic, while a fan of the Leeds-born striker, fears his progress could be stymied by Guardiola, a coach whom he famously failed to connect with at Barcelona.

"Can Guardiola make Haaland even stronger? It depends on Guardiola's ego, if he lets him become bigger than him or not," the Sweden international told Canal+.

"He didn't let me get bigger, me [and] others. Not only me, [but] many others [too]. I like Haaland, very much so. I think he is a very intelligent player. He doesn't do things he is not capable of."

Ibrahimovic also weighed in on the future PSG forward Mbappe, whose next step remains the subject of feverish speculation.

The France attacker penned an extension to stay with the Ligue 1 champions, turning down a move to Real Madrid, but has reportedly seen his working relationships subsequently break down at the club.

On whether he should have made the switch to LaLiga, Ibrahimovic added: "He made the right choice for Paris, not for himself.

"He put himself in a situation where is more important than the club. Then the club gave him the keys for that. But you are never bigger than a club."

Olivier Giroud scored twice and assisted two others as Milan sealed their place in the Champions League knockout stages with a comfortable 4-0 victory over Salzburg at San Siro on Wednesday.

Milan knew a point would be enough to secure their progression and Giroud's early headed finish set them on their way.

Giroud's brilliant assist allowed Rade Krunic to get on the scoresheet shortly after half-time before the former Chelsea striker fired home a loose ball in the box.

Junior Messias added further gloss late on as Milan registered consecutive Champions League wins for the first time since 2011 and eased into the knockout stages at Salzburg's expense.

Theo Hernandez almost put Milan in front inside three minutes but his low effort across goal hit the post and deflected wide.

The hosts took the lead after 14 minutes, Giroud powerfully nodding Sandro Tonali's corner into the back of the net with the help of sloppy Salzburg marking.

Giroud thought he had his second when he tapped home after Salzburg goalkeeper Philipp Kohn fumbled Hernandez's shot into his path, only for the offside flag to curtail his celebrations.

Krunic made it 2-0 just after half-time with an excellent header after Giroud deftly nodded Ante Rebic's delivery back across goal to set him up.

Giroud added another in the 57th minute, smashing home after the ball rebounded kindly to him in the box.

Rafael Leao should have scored a fourth for Milan when he was picked out with a superb Hernandez cross, but his first-time effort came back off the crossbar.

Substitute Messias' curled finish in injury-time was the final dagger to Salzburg's Champions League campaign, though, as Milan cruised through.

Stefano Pioli has signed a contract extension that will keep him at Milan until the end of the 2024-25 season.

The Rossoneri coach has been in position at San Siro since 2019, having previously taken charge of rivals Inter.

Pioli did not last long with the Nerazzurri, yet he has been a huge success with Milan, last season winning the Scudetto – their first since 2011.

The 57-year-old's deal was due to expire at the end of this campaign, but the club confirmed a two-year extension on Monday.

"Having begun this virtuous path, which led to the 2021-22 Serie A title, AC Milan and Stefano shall continue to work on this ambitious project, which reflects the club's history and values," a short statement added.

Pioli has won 87 of his 153 matches as Milan coach, with that 56.9 per cent win rate his best at any club.

Milan finished sixth in Serie A in Pioli's first season after he took over in the October, before jumping to second and then first in the subsequent campaigns.

Despite a shock defeat to Torino on Sunday, the Rossoneri are third this term.

Milan forward Ante Rebic has been left out of Croatia's preliminary 34-man squad for the upcoming World Cup in Qatar.

Rebic was a key part of the Croatia team who reached the World Cup final in Russia in 2018, opening the scoring in an impressive 3-0 group-stage win over Argentina in that tournament.

However, the Rossoneri man has only made three Serie A starts this season, and although he has hit the net three times in his seven total league appearances, it has not been enough to enter him into Zlatko Dalic's thoughts.

Rebic last played for his country at last year's Euro 2020.

Luka Modric briefly sparked concerns over his fitness when he missed Real Madrid's Champions League defeat to RB Leipzig this month, but the 2018 Ballon d'Or winner is included on the list, as are Chelsea's Mateo Kovacic and Tottenham's Ivan Perisic.

Croatia will begin their Group F campaign against Morocco on November 23, before facing Canada and Belgium, and they will name their final 26-man squad on November 9.

Croatia preliminary squad in full: Dominik Livakovic (Dinamo Zagreb), Ivica Ivusic (Osijek), Ivo Grbic (Atletico Madrid), Dominik Kotarski (PAOK), Nediljko Labrovic (Rijeka); Domagoj Vida (AEK), Dejan Lovren (Zenit), Borna Barisic (Rangers), Duje Caleta-Car (Southampton), Josip Juranovic (Celtic), Josko Gvardiol (RB Leipzig), Borna Sosa (Stuttgart), Josip Stanisic (Bayern Munich), Marin Pongracic (Lecce), Martin Erlic (Sassuolo), Josip Sutalo (Dinamo Zagreb); Luka Modric (Real Madrid), Mateo Kovacic (Chelsea), Marcelo Brozovic (Inter), Mario Pasalic (Atalanta), Nikola Vlasic (Torino), Luka Ivanusec (Dinamo Zagreb), Lovro Majer (Rennes), Kristijan Jakic (Eintracht Frankfurt), Luka Sucic (Salzburg), Josip Misic (Dinamo Zagreb); Ivan Perisic (Tottenham), Andrej Kramaric (Hoffenheim), Josip Brekalo (Wolfsburg), Bruno Petkovic (Dinamo Zagreb), Mislav Orsic (Dinamo Zagreb), Ante Budimir (Osasuna), Marko Livaja (Hajduk Split), Antonio Colak (Rangers).

Milan failed to move back within three points of Serie A leaders Napoli as goals from Koffi Djidji and Aleksey Miranchuk condemned the Rossoneri to a surprise 2-1 loss to Torino.

Miranchuk followed up Djidji's glancing header with a cultured left-footed finish as Torino scored twice in two frantic first-half minutes to stun Milan at the Stadio Olimpico Grande Torino.

Stefano Pioli's men travelled to Turin looking to stay within touching distance of the Serie A summit, but were uncharacteristically lethargic for long periods on Sunday.

Junior Messias was gifted a goal following a bizarre mix-up at the back, but Milan failed to build on that strike late on as Torino clung on for a huge win.

Rafael Leao missed two golden chances in the first six minutes, sending a wild volley over after breaking in behind before mishitting his shot after being teed up by Brahim Diaz.

Torino punished Milan for their wastefulness 10 minutes before the break, as Djidji nodded Valentino Lazaro's deep free-kick in off the right-hand post.

Things quickly went from bad to worse for the champions as Miranchuk latched onto Nikola Vlasic's knock-down before shifting the ball onto his left foot and finishing coolly across Tatarusanu. 

Sergino Dest fired over from range as Milan attempted to lift the tempo after the break, before Messias ensured a tense finish when he curled home following a clash between Vanja Milinkovic-Savic and Perr Schuurs.

Torino boss Ivan Juric was dismissed for berating referee Rosario Abisso following that goal, but his team showed greater composure to see out the closing stages in relative comfort.

What does it mean? Rossoneri fall short

Although the likes of Napoli and Atalanta have made headlines in Serie A by emerging as surprise pacesetters, Milan had begun their title defence in solid fashion, stretching their unbeaten away run to 17 league games ahead of Sunday's contest (W12 D5).

Milan had also kept five consecutive clean sheets in league meetings with Torino prior to this game, but they saw both of those records fall by the wayside after a quickfire double from their hosts, who richly deserved the win following a disciplined performance.

Djidji ends barren run

To say Torino have struggled against Milan in recent meetings would be an understatement: Djidji's opener ended a 499-minute run in which Torino had failed to find the net against Milan in Serie A meetings.

Their previous goal against the Rossoneri in the competition was scored by Andrea Belotti in September 2019, and prior to Sunday's game, no player in Torino's current squad had scored a league goal against Milan.

Leao kept quiet

Leao has emerged as the most obvious goal threat in an exciting Milan team, having recorded nine league goal contributions (five goals, four assists) ahead of the trip to Turin.

However, the Portugal attacker was hauled off at the break after a disappointing first half in which he squandered chances amounting to 0.51 expected goals (xG) and failed to hit the target with any of his four attempts.

What's next?

Milan host Salzburg in the Champions League on Wednesday, needing to avoid defeat to reach the last 16. Torino, meanwhile, go to Bologna in Serie A next Sunday.

Chelsea are reportedly the latest Premier League club to signal their interest in 25-year-old Inter striker Lautaro Martinez.

Martinez, who has also scored 21 senior goals for Argentina in 40 international appearances, is coming off a career-best season in the Serie A.

He set a new personal-best with 21 league goals in 35 games in 2021-22, and has started this season in similar fashion, netting six times in 11 Serie A fixtures.

Martinez also showed his quality with a goal and an assist in the dramatic 3-3 Champions League draw against Barcelona.

TOP STORY – CHELSEA LOOK TO INTER FOR STRIKER SOLUTION

According to InterLive, what separates Chelsea's chances from Martinez's other Premier League suitors is their potential to include current loanee Romelu Lukaku in their bid.

The report states Inter's starting point for an acceptable price tag will be €90million, which is what Tottenham are said to have offered before the beginning of last season.

Tottenham are one of the other Premier League teams named in the report, while Manchester United and Newcastle United have previously been connected with a pursuit of Martinez.

Inter will have all the leverage in any negotiations, with Martinez's contract tying him to the club until 2026.

ROUND-UP

– De Telegraaf claims PSV are in such a dire financial situation that they will be forced to accept a €30m bid for 23-year-old breakout star Cody Gakpo. 

– According to Calciomercato, Arsenal, Newcastle and West Ham are all circling 21-year-old Midtjylland winger Gustav Isaksen.

– Diario Sport is reporting Paris Saint-Germain are the favourites to land prized 16-year-old Palmeiras prospect Endrick, while Real Madrid are also said to be all-in, and Barcelona may turn their attention to more pressing matters.

– Spezia are looking for €30m to part ways with 22-year-old centre-back Jakub Kiwior, with Milan, Juventus and West Ham said to have strong interest, per Tuttomercatoweb.

– The Chronicle is reporting Newcastle are weighing up a move for 18-year-old winger Eguinaldo, who plays for Vasco Da Gama in the Brazilian second division and has a £26m release clause in his contract.