Champions League last-16 draw: tie-by-tie analysis

Liverpool v Real Madrid

Last month, Real Madrid’s president, Florentino Pérez, advocating for a Super League, lamented that his club have faced Liverpool in just nine competitive games. His wish for more has been granted sooner than he expected and perhaps would have liked. Real beat Liverpool reasonably comfortably in last season’s final and had few issues topping a relatively straightforward group, while Liverpool have suffered a miserable start to the season. With Mohamed Salah returning to form, though, Jürgen Klopp’s side may have improved by February and, out of the title race, can afford to focus on Europe. Aurélien Tchouaméni has joined Real and Eduardo Camavinga was beginning to make an impact last season, but the sense remains that the post-Casemiro midfield is yet to be really tested.

Winners Liverpool.

RB Leipzig v Manchester City

These teams met in last season’s group stage, City winning 6-3 at the Etihad before a 2-1 defeat in Germany, with qualification long since secured. In the first of those games, Leipzig were managed by Jesse Marsch; in the second by the caretaker Achim Beierlorzer. Since then Domenico Tedesco has come and gone and now, under Marco Rose, there has been a significant upturn. Saturday’s 3-1 win at Hoffenheim extended Leipzig’s unbeaten run to 11 games and they have been prolific in that time. The front four of André Silva, Dominik Szoboszlai, Christian Nkunku and Timo Werner, who should be back from his ankle injury by February, will test City on the counter.

Winners Manchester City.

Club Brugge v Benfica

Club Brugge were the great surprise of the group stage, winning their first three games without conceding a goal. They secured progress with a 0-0 draw at Atlético Madrid, but the heavy home defeat to Porto that ultimately cost them top spot perhaps gave a truer impression of their abilities: no pushovers, well-organised, but essentially limited. Benfica, meanwhile, ended the group stage in joyous form, with Rafa Silva and João Mario playing probably the best football of their careers. There may be defensive concerns but, even more than the 6-1 win at Maccabi Haifa that meant they topped the group, the 4-3 win over Juventus, when they should have won far more convincingly, demonstrated just how dangerous Roger Schmidt’s side can be.

Winners Benfica.

Milan v Tottenham

Tottenham have not lost to Milan in their four previous meetings, a Peter Crouch goal giving them a 1-0 win at San Siro in their last tie in 2010-11, but how good they are at the moment is anyone’s guess. Hampered by injuries to forwards, with a weird inability to play in the first half (particularly when Dejan Kulusevski is absent) and a dislocation between the midfield and the forward line, their results have been rather better than performances so far this season. The Italian champions have suffered only two defeats in Serie A and have in Rafael Leão one of the more exciting forwards in Europe, but they were desperately poor in losing twice to Chelsea during the group stages, with injuries offer only some excuse.

Winners Tottenham.

Eintracht Frankfurt v Napoli

Top of Serie A, unbeaten domestically and hugely impressive in the group stage, Napoli may be the most serious Italian challengers since Juventus decided five league titles in five seasons just wasn’t good enough and got rid of Massimiliano Allegri. They are playing fast, dynamic football under Luciano Spalletti and, after the failure of Italy, Nigeria and Georgia to qualify for the World Cup, have an unusual number of players who should be refreshed by a winter break. But unfancied as they may be under Oliver Glasner, Eintracht Frankfurt have become masters of the European away leg. Their Europa League success last season featured victories at Real Betis, Barcelona and West Ham, and this season they won on the road against Marseille and, when they absolutely needed it, Sporting.

Winners Napoli.

Borussia Dortmund v Chelsea

After a shaky start, progress from the group ended up being straightforward for Chelsea, but this is a club still undergoing transition as the recent league defeats to Brighton and Arsenal have shown. There were problems to be addressed in the squad even before the complications of sanctions, and recent injuries have exposed the imbalances that Graham Potter will need to resolve. With Sevilla in miserable form, Borussia Dortmund qualified for the last 16 easily enough, thanks in no small part to a 4-1 win in Spain, a game that highlighted just how important Jude Bellingham has become to Alen Terzic’s side. He may be only 19 but only he, Julian Brandt and Nico Schlotterbeck have played all 13 league games for their club this season.

Winners Chelsea.

Internazionale v Porto

Porto trail Benfica by eight points domestically but they showed admirable resolve to bounce back from successive defeats at the start of the group stage to qualify with four wins in a row. After suffering a knee injury a month ago, Pepe is a doubt for the World Cup but Porto should have his experience back at the heart of the defence for the last 16. This has not been an easy season domestically for Internazionale and they were twice well-beaten by Bayern Munich, but two fine counterattacking performances against Barcelona ensured progress to the knockout phase for only the second time in the past decade. If Romelu Lukaku can rediscover his form and fitness, his partnership with Lautaro Martínez represents a major threat.

Winners Porto.

Paris Saint-Germain v Bayern Munich

For most of the group stage Paris Saint-Germain seemed to be cruising to top spot, but they were undone at the last by Benfica’s flurry away to Maccabi Haifa and are punished with a repeat of the 2020 final. In a sense they fell into a trap they had dug themselves by drawing at home against Benfica the day after stories broke of Kylian Mbappé’s supposed unhappiness at the club. The competing egos will always be the biggest challenge for a PSG coach. Bayern are top of the Bundesliga again, but four draws and a defeat at Augsburg have led to a certain amount of chuntering about Julian Nagelsmann, despite six wins out of six in the Champions League. His record in big European games is not brilliant.

Winners Bayern Munich.