Arsenal have been drawn against Bayern Munich in the last 16 of the Champions League, with Man City to face Monaco and Leicester to play Sevilla.
The Gunners would have been hoping for an easier tie after winning their group for the first time in five seasons, but will face one of Europe’s top clubs after Bayern qualified for the knockout stage by finishing second in Group D.
Arsenal were eliminated by Bayern at this stage of the competition in both 2013 and 2014, and the two sides also met in the group stages last season.
Premier League champions Leicester are the only round-of-16 debutants and are likely to be given a tough test by hardened European campaigners Sevilla, who have won the Europa League for the last three seasons.
Manchester City reached the semi-finals last year and will continue their campaign against Monaco, who beat Tottenham home and away on their way to winning Group E.
Holders Real Madrid will take on Italian side Napoli and there will also be a heavyweight clash between Barcelona and Paris Saint-Germain, the reigning champions of Spain and France.
Italian champions Juventus will take on Porto, Portuguese champions Benfica have been handed a tough tie against Borussia Dortmund and Atletico Madrid, who have been beaten finalists in two of the last three seasons, will play Bayer Leverkusen.
The draw for the UEFA Champions League Round of 16:
Man City v Monaco
Real Madrid v Napoli
Benfica v Borussia Dortmund
Bayern Munich v Arsenal
FC Porto v Juventus
Bayer Leverkusen v Atletico Madrid
PSG v Barcelona
Sevilla v Leicester
Ties to be played 14/15 & 21/22 February and 7/8 & 14/15 March.