Arsenal face a tricky tie against Benfica in the Europa League last-32 but there was better news for Tottenham, who take on Austrian side Wolfsberg.
Manchester United’s ‘reward’ for dropping out of the Champions League is a tough meeting with Real Sociedad, who are flying high in La Liga.
Leicester City will take on Slavia Praha after topping their group, while Rangers will meet Royal Antwerp, who finished second to Spurs during the group stage.
Among the other standout ties are Lille facing European giants Ajax and Salzburg taking on Villarreal.
These ties will be played on February 18, with the return legs a week later of February 25.
The exception is Tottenham’s second leg against Wolfsberger, which will be played on February 24 to avoid a clash with Arsenal’s home game on the same night.
The draw in full:
Seeded teams: Ajax, Arsenal, AC Milan, Tottenham, Leicester City, Manchester United, Napoli, PSV Eindhoven, Rangers, Bayer Leverkusen, Villarreal, Shakhtar Donetsk, AS Roma, Hoffenheim, Dinamo Zagreb, Club Brugge
Unseeded teams: Red Star, Krasnodar, Dynamo Kyiv, Olympiacos, RB Salzburg, Young Boys, Molde, Slavia Prague, Benfica, Granada, Real Sociedad, Braga, Lille, Maccabi Tel-Aviv, Antwerp, RZ Pellets WAC
Wolfsberger vs Tottenham
Dynamo Kyiv vs Club Brugge
Real Sociedad vs Man United
Benfica vs Arsenal
Red Star vs AC Milan
Antwerp vs Rangers
Slavia Praha vs Leicester
Salzburg vs Villarreal
Braga vs Roma
Krasnodar vs Dinamo Zagreb
Young Boys vs Leverkusen
Molde vs Hoffenheim
Granada vs Napoli
Maccabi Tel-Aviv vs Shakhtar Donetsk
Lille vs Ajax
Olympiacos vs PSV