Last season’s Champions League finalists Real Madrid and Liverpool have been paired together in this season’s last-16.
The Reds finished runners-up in their group behind Napoli and will host the reigning European and LaLiga champions at Anfield in February.
Real beat the Reds 1-0 in the 2022 final in Paris in May, a match marred by organisational chaos which led to the kick-off being delayed.
Premier League champions and 2021 Champions League finalists Manchester City have been drawn to face German side RB Leipzig – fourth in last season’s Bundesliga – in the last 16.
Tottenham, who sealed top spot in their group with a last-gasp winner from Pierre-Emile Hojbjerg away at Marseille, have been drawn to face Italian champions AC Milan with the first leg at San Siro.
Chelsea, winners of the competition in 2012 and 2021, will be up against Bundesliga runners-up Borussia Dortmund in the round of 16.
The first leg ties will be played on February 14th, 15th, 21st and 22nd, with the second legs on March 7th, 8th, 14th and 15th.
German champions Bayern Munich – who did not drop a point in the group phase – are up against French league champions Paris St Germain, who they beat in the 2020 final of the competition.
Inter Milan, who finished runners-up behind Bayern in Group C, face Portuguese champions Porto while Club Brugge take on Benfica.
Europa League winners Eintracht Frankfurt will go up against Napoli for a place in the quarter-finals.
In the Europa League, Manchester United have been drawn against Barcelona in the knockout play-off round.
The Catalan giants have dropped down into the competition after failing to get out of their Champions League group, but now provide a stern test for Erik ten Hag’s Red Devils who finished second in their Europa League group.
United will travel to the Nou Camp on February 16th for the first leg of the tie, with the return at Old Trafford taking place on February 23rd.
The Red Devils have some fond memories of the Nou Camp, having completed the 1999 treble in the stadium with a last-gasp victory over Bayern Munich in that year’s Champions League final.
Arsenal, who won their Europa League group, have already progressed to the last 16 of the competition.
Champions League last-16 draw
RB Leipzig vs Manchester City
Club Brugge vs Benfica
Liverpool vs Real Madrid
AC Milan vs Tottenham Hotspur
Frankfurt vs Napoli
Borussia Dortmund vs Chelsea
Inter Milan vs Porto
PSG vs Bayern Munich
Europa League knockout play-off draw
Barcelona v Manchester United
Juventus v Nantes
Sporting Lisbon v Midtjylland
Shakhtar Donetsk v Stade Rennais
Ajax Amsterdam v Union Berlin
Bayer Leverkusen v AS Monaco
Sevilla v PSV Eindhoven
Salzburg v AS Roma
