Arsenal have been drawn to face Bayern Munich in the Champions League last 16, while Paris Saint-Germain will take on Barcelona.
Holders Real Madrid are up against Napoli and Leicester City will come up against Sevilla.
Pep Guardiola’s Manchester City are to play Monaco and Italian champions Juventus face Porto.
Borussia Dortmund are set to do battle with Benfica, while Bayer Leverkusen have a tough test having been picked out against Atletico Madrid.
Arsene Wenger would have hoped for a favourable opponent after his side beat PSG to top spot in Group A, but instead Arsenal face Bayern for the fourth time in five seasons.
Bayern put Arsenal out of the competition at the last 16 in 2013 and 2014, while they met in the group stages of last season’s competition.
PSG meet Barca in the other standout tie from Monday’s draw in Nyon.
Unai Emery’s men know Barca all too well – they lost to them in the 2013 and 2015 quarter-finals as well as doing battle in the 2014 group stage.
Guardiola has never failed to reach the semi-finals in seven seasons as a Champions League head coach and he will be hopeful of getting the better of Monaco, who topped the group that saw Tottenham eliminated.
Leicester’s hopes of extending their European stint will rest on their success against a team with impressive continental pedigree in Sevilla – Europa League winners for each of the last three seasons.
The last-16 draw in full, first-leg ties to be played February 14-15 and 21-22:
Manchester City v Monaco
Real Madrid v Napoli
Benfica v Borussia Dortmund
Bayern Munich v Arsenal
Porto v Juventus
Bayer Leverkusen v Atletico Madrid
Paris Saint-Germain v Barcelona
Sevilla v Leicester City