Tottenham have been drawn against Wolfsberger in the last 32 of the Europa League.
Jose Mourinho’s side will head to Austria in February having won Group J.
Manchester United will head to Real Sociedad for the first leg of their last 32 tie having been paired together after United were knocked out of the Champions League last week.
Arsenal will play Benfica with Mikel Arteta’s side having topped Group B.
Rangers will play Royal Antwerp, with Steven Gerrard’s side having won Group D ahead of Benfica.
Leicester have been drawn against Slavia Prague in the last 32 and will travel to the Czech Republic for the first leg.
Following is the draw for the Europa League round of 32 made on Monday:
Wolfsberger AC v Tottenham Hotspur
Dynamo Kyiv v Club Brugge
Real Sociedad v Manchester United
Benfica v Arsenal
Red Star Belgrade v AC Milan
Royal Antwerp v Rangers
Slavia Prague v Leicester City
RB Salzburg v Villarreal
Braga v AS Roma
Krasnodar v Dinamo Zagreb
Young Boys v Bayer Leverkusen
Molde v Hoffenheim
Granada v Napoli
Maccabi Tel-Aviv v Shakhtar Donetsk
Lille v Ajax Amsterdam
Olympiakos v PSV Eindhoven
First legs to be played on Feb. 18. Second legs to be played on Feb. 25.
The draw for the round of 16 will take place on Feb. 26.