Manchester United will face Paris Saint-Germain in the Champions League round of 16, while Liverpool have been drawn against Bayern Munich.
Atletico Madrid take on Juventus, Tottenham are up against Borussia Dortmund and Real Madrid face Ajax.
Barcelona play Lyon, Manchester City meet Schalke, while AS Roma vs Porto completes the last-16 ties.
The first legs will take place on 12-13 and 19-20 February, with the return fixtures on 5-6 and 12-13 March.
Group winners will be away from home in the first legs.
Teams could not be drawn against sides from the same country in the last 16, nor against teams who they played in the group stage.
Three-time European champions Manchester United have never met PSG, who were the top scorers in the groups, in a competitive game.
The Ligue 1 champions advanced to the knockout stage despite defeat at Liverpool in their opening match.
Despite dominating the French domestic game in recent years, the Qatari-owned club have never progressed past the quarter-finals of the Champions League.
Ajax vs Real Madrid
Liverpool vs Bayern Munich
Manchester United vs PSG
Lyon vs Barcelona
Tottenham vs Dortmund
Schalke 04 vs Manchester City
AS Roma vs FC Porto
Atletico Madrid vs Juventus