Napoli vs Barcelona
Barcelona have not reached the final of the Champions League since their most recent triumph in 2015, and second-leg collapses against Roma and Liverpool in the last couple of seasons mean the pressure is on the Catalan giants to deliver in 2019/20.
Napoli did well to negotiate a potentially tricky group under Carlo Ancelotti, but it is still too early to tell how they will shape up under new boss Gennaro Gattuso. Regardless, it is hard to see the Italian outfit denying Barcelona victory over two legs.
Chelsea vs Bayern Munich
A re-run of the 2012 Champions League final pits Chelsea against Bayern Munich. The Blues progressed from arguably the most open group this season, qualifying for the knockout phase alongside Valencia and ahead of Ajax and Lille, while Bayern romped home with six wins and maximum 18 points.
Even during their positive runs, Chelsea have looked defensively susceptible under Frank Lampard in 2019/20. That could prove their undoing against Bayern, who have not been at their best in the Bundesliga but are nevertheless favourites to triumph in this matchup.
Tottenham vs RB Leipzig
Tottenham may have avoided a traditional European heavyweight in the last-16 draw, but this tie will not be straightforward by any means. RB Leipzig have made magnificent progress in recent years and currently sit atop the Bundesliga table under the guidance of the impressive Julian Nagelsmann.
Jose Mourinho will hope that Spurs’ superior experience will help them through to the last eight, but a Leipzig triumph would not be a shock in the way many fans in England may assume.
Lyon vs Juventus
Juventus made light work of the group stage, finishing in first place ahead of Atletico Madrid and Bayer Leverkusen. They will be very pleased with this draw too, and it is no surprise that their odds to win the Champions League have shortened after being paired with Lyon.
The French outfit are not a bad side on their day, but Juve will not fear a team currently languishing in eighth place in France’s Ligue 1 table, just three points above Brest in 15th. Barring complacency, this should be a pretty comfortable win for Maurizio Sarri’s men.
Atletico Madrid vs Liverpool
Provided they maintain a healthy lead in the Premier League title race, there is no reason why Liverpool should slow down in Europe. Jurgen Klopp’s side have every chance of retaining the trophy they won with victory over Tottenham at Atletico Madrid’s Wanda Metropolitano stadium in May.
Diego Simeone’s side have had some teething problems after a squad overhaul in the summer, but they will still be a tough nut for Liverpool to crack.
Atalanta vs Valencia
Atalanta were on the brink of an early elimination after collecting just one point from their first four group-stage encounters, but back-to-back victories saw them advance to the last 16 alongside Manchester City.
Valencia changed their manager at the start of the season but responded well to qualify as group winners ahead of Chelsea, Ajax and Lille. This could be one of the tightest ties of the first knockout round.
Real Madrid vs Manchester City
Real Madrid have won three of the last four Champions Leagues, and although they have clearly dropped off in the last couple of seasons, they will still pose a stern test for Manchester City in the last 16.
Nevertheless, Pep Guardiola’s side have the quality to beat Madrid if they are at their best. They have struggled defensively at times this season but should be able to overcome Zinedine Zidane’s charges over two legs.
Borussia Dortmund vs Paris Saint-Germain
PSG now take the Ligue 1 title for granted, which means the success (or otherwise) of their season will once again be defined in the Champions League. They got off to a promising start in the group stage, but Thomas Tuchel will know that the knockout phase is where he will be judged.
Dortmund remain an inconsistent team, which makes this a difficult tie to call. Whoever ultimately progresses, we can expect a fair few goals in both legs.