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Liverpool and Manchester United were both handed nightmare draws in the first knockout rounds of the Champions League and Europa League as they were paired against Real Madrid and Barcelona.
Liverpools meeting with Real will be a repeat of last seasons final, which Jurgen Klopps side lost 1-0 after starting the game as favourites.
It is not the Round of 16 tie either Klopp or Real manager Carlo Ancelotti would have wanted and defeat would be a major blow for both given they are teams expected to reach the latter rounds.
It is also the price Liverpool pay for finishing second behind Napoli in Group A, which was largely caused by the 4-1 defeat they suffered in Naples in the opening round of fixtures back in September.
Klopp, though, tried to put a positive spin on the draw, insisting it was the sort of game that should excite rather than worry supporters and players alike.
The first thing that we can say about this draw is it is proper Champions League. Klopp told . This is a tie that speaks for itself and one that we should all be excited about.
I know we have played Real Madrid in a couple of recent finals but it is not so often that our two clubs have met in a two-legged tie so now we can look forward to this happening.
Reals European record is the best around. We know this. But we also know that ours is not too bad. On top of this, we know that we have Anfield and everyone knows what this means.
It is a really good draw. A really exciting draw. The games themselves are still a few months away but it does not take a great deal of imagination to think what the atmosphere will be like at both games.
There is a lot of football to be played before this, of course, so we will focus on each game as it comes but yes, this draw has given us something special to look forward to.
Uniteds worst case scenario also came true after they failed to score a second goal in the 1-0 win over Real Sociedad last week that meant they finished second in their Europa League group too.
That forced them into a Europa League play off against one of the teams dropping into the competition from the Champions League.
Barcelona only managed to secure third spot behind Bayern Munich and Inter Milan in Group C, losing three of their six games, with just two wins over Czech side Plzen to show for their efforts.
But Barca are still top of La Liga, albeit having played a game more than Real Madrid, and have a strong side on paper. They will also be highly motivated to do well in the Europa League given their Champions League failure, although manager Xavi was less than enthused about having to face Erik ten Hags side.
It is the most difficult opponent once again, he told ESPN. But we will look forward to it. They are a historic side, they have grown a lot with the arrival of Ten Hag, they have great players. Its the worst draw we could have got. Once again. No luck.
There was a kinder looking draw for Premier League champions Manchester City, who will take RB Leipzig. The German side won four games in a row to finish second behind Real Madrid and beat City in a dead rubber clash in the group stages last season, but Pep Guardiolas side should be too strong for a team sitting sixth in the Bundesliga this time.
Tottenham Hotspur manager Antonio Conte will be relishing a return to Italy to take on AC Milan, having enjoyed success as the manager of Inter. Spurs also have an excellent chance of progressing against the Serie A champions given they were beaten home and away by Chelsea in the group stage.
As for Graham Potters stumbling side, they will take on Borussia Dortmund and will have to rediscover their form before then against a side only narrowly beaten by Man City at the Etihad before securing a draw in Germany to secure second place in the group.
The other mouthwatering tie in the first knockout round is the clash between Paris Saint Germain and Bayern Munich, who were also considered among the favourites to win the Champions League back in August.
Paris Saint Germain, like Manchester City, have so far failed to convert dominance of their domestic league into a European Cup and could easily suffer another early exit at the hands of the German champions.
City will be pleased with this draw. Yes, Leipzig won four games in a row to finish second behind Real Madrid in Celtics group and have a host of exciting young players not least Christopher Nkunku and Josko Gvardiol, both wanted by Chelsea and have also added more experience. But City should prove far too strong. Nevertheless Leipzig are dangerous and beat City in the group stages last season and also scored three times (Nkunku hat-trick) at the Etihad.
Perhaps two surprise packages with Benfica having shocked Paris Saint-Germain by finishing above them in their group. By dint of that, and playing the second leg at home, and their European pedigree they will go into this tie as favourites. However there was little expectation that Brugge would reach this stage and they cannot be discounted with striker Ferran Jutgla a rising star.
A reprise of last seasons final and a chance for revenge. But it feels like a punishing draw for Liverpool given they gained 15 points and yet finished second in the group stages. Despite Liverpools struggles this season and despite Reals imperious form it is a 50:50 game. But the fact the second leg is at the Bernabeu, where the Spaniards also appear to pull it off, tips it in Madrids favour. Just.
Antonio Conte the former Inter Milan coach - will relish a return to Italy and to the San Siro. He will also fancy Tottenhams chances of progressing. Milan are the Serie A champions but are inexperienced and lost home and away to Chelsea. It will be close but Conte has to finally improve that appalling record in European knock-out ties and Spurs will recall the 2011 meeting with Joe Jordan and Gennaro Gattuso clashing on the pitch.
The Italians were the top-scorers in the group stage and were a team that everyone else wanted to avoid. If they maintain their form they will be one of the favourites to win the Champions League, never mind this tie. Even so Frankfurt should not be under-estimated after finished above Sporting and Marseille in the tightest of groups.
Another evenly balanced tie with Dortmund having acquitted themselves well in Manchester Citys group where they were unfortunate to lose away. For them it is all about Jude Bellingham, who scored in four successive games, with the added interest that Chelsea are among their suitors. Again it could be tight but Chelsea to edge it even if both teams appear to be works-in-progress.
Although Porto won their group with Atletico Madrid imploding and finishing bottom - they will go into this as underdogs against Inter who, of course, knocked out Barcelona in the toughest of groups. Still it has been a tricky campaign for Inter who have struggled domestically and with Romelu Lukaku having a torrid time through injury.
PSG have built their squad to win the Champions League and yet still no-one quite knows how they will do especially with their stars Lionel Messi, Neymar and Kylian Mbappe being so geared up towards the World Cup. Bayern breezed their group but, overall, have been a bit patchy and despite scoring lots of goals have not replaced Robert Lewandowski.
Barcelona coach Xavi Hernandez called this the worst possible draw for his club. The feeling will be mutual at United. Even so Barcelona, top of La Liga and with a formidable attack, will be the favourites and should go through. Their vulnerability is in central defence but they are expected to remedy that in the January window. A really tough draw for United.
Manchester City faced Leipzig twice in last seasons Champions League group stage, winning 6-3 at home and losing 2-1 away.
Liverpool and Real Madrid have played each other nine times. Despite winning the first three games, the English side are winless in six matches against the holders.
Perhaps some good omens for Spurs: they have never lost to AC Milan in four meetings and Milan have lost nine of their last 11 Champions League matches against English opposition.
This will be the first time that Chelsea and Borussia Dortmund have played each other. Dortmund have lost eight of their last nine Champions League fixtures against English opposition.
Manchester United will play Barcelona in a re-run of the 2009 and 2011 Champions League finals. Barcelona finished behind Bayern Munich and Internazionale in their Champions League group and are top of La Liga, although Real Madrid have a game in hand.
Their squads boasts significant talents, including Poland striker Robert Lewandowski and Golden Boy winner Gavi.
United may fancy their chances as Barcelona didnt beat Inter or Bayern in the Champions League group stages.
The Austrians go up against the inaugural Europa Conference League winners.
A big clash as six-time winners Sevilla take on the Ruud van Nistelrooys PSV.
The Germans go up against the Ligue 1 side.
The 2019 Champions League semi-finalists take on the Bundesliga high-fliers.
The team from the Donbas, who are playing their home games in Poland, will take on the Brittany club.
The Portuguese take on the Danish side.
The Italian big hitters play the French side.
Manchester United to play five time Champions League winners Barcelona
Ex-Hungary midfielder Zoltan Gera joins Uefa deputy general secretary Giorgio Marchetti for the draw.
Gera was part of the Fulham team which reached the 2010 Europa League final.
Manchester United are the only English side involved in the Europa League play-off draw, as Arsenal qualified for the last 16 after winning their group.
Manchester United could have a tough tie, as they can be drawn against Ajax, Barcelona, Bayer Leverkusen, Sevilla, Sporting CP, Juventus, Salzburg or Shakhtar Donetsk.
All eyes will be on 19-year-old midfielder Jude Bellingham as 1997 Champions League winners Dortmund take on Chelsea. Set to go to the World Cup with England, the teenager is one of Dortmunds star players and Chelsea are one of the many clubs reported to be interested in signing him.
Although they will be glad to have missed PSG, this will not be an easy tie for Chelsea, as the German club drew with Man City in the group stages. Fourth in the Bundesliga and only three points from the top of the table, Dortmund are having a decent season.
Not an easy draw for Tottenham, as they face AC Milan in the last 16. The Italians had a decent group stage, despite being beaten relatively easy by Chelsea on both occasions. They confirmed their place in the knockout stages with 4-0 wins of Dinamo Zagreb and RB Salzburg.
Englands Fikayo Tomori will be one to watch. The centre-back has been a regular since joining in 2021 and helped Milan to the league title last year. He was sent off against Chelsea at the San Siro in the group stage, so may have a point to prove against another London club.
Manchester City should be reasonably happy after being drawn against RB Leipzig. The German side started their Champions League campaign poorly, losing their first two matches, but then went on a hot streak and won their final four games, including a 3-2 victory over Real Madrid.
They seem to have improved under Marco Roses management, having been beaten in the Europa League semi-final by Rangers last season.
City should beware of Christopher Nkunku and Dominik Szoboszlai, who both impressed against Celtic in the group stage.
Liverpool face the toughest draw of all the English teams as they go up against 14-time winners Real Madrid in a re-run of Mays Champions League final.
Vinicius Junior scored the only goal of the game in Stade de France. Real Madrid also beat Liverpool 3-1 in the 2018 final, with two screamers from Gareth Bale and a poor performance from Liverpool goalkeeper Loris Karius.
The Kingsley Coman derby will take place as the two European big-hitters go head-to-head.
The Italian giants take on the Portuguese side.
The West London club will take on the 1997 winners.
The Europa League winners have a tough tie in southern Italy.
The North London side will be taking on the north Italians in the round of 16.
The six-time winners take on Real Madrid in a re-run of last years final.
The Belgian side will take on the Portuguese team
The English champions will play the 2020 semi-finalists
Former Turkey midfielder Hamit Altintop, who played for Bayern Munich and Real Madrid, will be helping Uefa Deputy General Secretary Giorgio Marchetti with the draw.
Standing next to the Champions League trophy, host Pedro Pinto has welcomed viewers to the draw.
All of the English teams face a potentially difficult draw. Liverpools options are less favourable, after they finished behind Napoli in their group. They will be hoping to avoid Real Madrid or Bayern Munich, with the possibility of also playing Porto or Benfica.
Manchester City, Chelsea and Tottenham will all be looking to avoid PSG, who are the strongest of their potential opponents. They could also have difficult ties against Inter Milan, RB Leipzig or Club Bruges.
Manchester City and Tottenham could also play AC Milan, while Manchester City and Chelsea could draw Eintracht Frankfurt. Chelsea and Tottenham could also play Borussia Dortmund.
Some big teams missed out on the knockout stages of the Champions League this year.
Ajax finished behind Napoli and Liverpool in Group A, while Atletico Madrid finished bottom of Group B, with Porto and Club Bruges progressing.
Barcelona are in the Europa League after finishing third in Group C behind Bayern Munich and Inter Milan, with Juventus also in Europes second competition, after Benfica and PSG finished ahead of them in Group H.
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With just under 40 minutes until the draw starts, here is a reminder of the group winners and runners-up.
Group winners: Napoli, Porto, Bayern Munich, Tottenham, Chelsea, Real Madrid, Manchester City, Benfica
Runners-up: Liverpool, Club Bruges, Inter Milan, Eintracht Frankfurt, AC Milan, RB Leipzig, Borussia Dortmund, PSG
A full quota of four Premier League clubs wait to discover their Champions League fate at todays last-16 draw, with Paris Saint Germain lurking among the teams who finished second in their group.
Tottenham, Manchester City and Chelsea will be hoping to avoid the French side, with Liverpool facing a 50:50 chance of drawing Real Madrid or Bayern Munich.
So much can change between the draw and matchday in February, especially in this unprecedented season which is split in half by the Qatar World Cup.
Here is a reminder of the English clubs possible opponents:
Manchester City: Inter Milan, Eintracht Frankfurt, RB Leipzig, AC Milan, Club Brugge, PSG
Chelsea: Inter Milan, Eintracht Frankfurt, RB Leipzig, Borussia Dortmund, Club Brugge, PSG
Tottenham: Inter Milan, AC Milan, RB Leipzig, Borussia Dortmund, Club Brugge, PSG
Liverpool: Porto, Real Madrid, Bayern Munich, Benfica
Pep Guardiola will be hoping this is the season Manchester City finally lift the Champions League, after losing in the final two seasons ago and collapsing in dramatic fashion against Real Madrid last year.
Chelsea, Tottenham and Liverpool are all in a battle to finish in the top four of the Premier League, so could view a strong run in the Champions League as a route back into the competition.
Graham Potter will hope to have Reece James, Ben Chilwell and Wesley Fofana back after the break, and possibly NGolo Kante, which could make Chelsea a far more competitive outfit. Tottenham have also been without Dejan Kulusevski and Richarlison in recent weeks, and despite question marks over their performances they have the firepower to chin any opponent in knockout football. Liverpools domestic form has been startlingly poor, but they have previous for saving their best stuff for Europe and remain a formidable force at Anfield.
None of the English teams can draw each other in this round, but can do so from the quarter-finals onwards.
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