Manchester United were drawn against Real Sociedad in the Europa League round of 32, while Arsenal will take on Benfica.
United dropped into the Europa League following their elimination from the Champions League at the group stage and face a tricky clash against the La Liga leaders.
The two sides met in the group stage of the Champions League in 2013-14, with United winning 1-0 at Old Trafford as well as drawing 0-0 at Anoeta.
Former United academy graduate Adnan Januzaj will return to Old Trafford for the first time since leaving the club in 2017.
Arsenal and Benfica are facing off for the first time since 1991, when the Portuguese side knocked the Gunners out in the second round.
Two former European champions meet in Red Star Belgrade and AC Milan, while Roma face a tricky trip to Braga. Tottenham will take on Austrian side Wolfsburger, who have reached the Europa League knockout phase for the first time. The first legs will be on Feb. 18 with returns on Feb. 25
Holders Sevilla will not defend their trophy as they are in the Champions League round of 16, while last season's runners-up Inter Milan were eliminated from Europe's premier competition at the group stage.
Europa League round of 32 draw
Wolfsburger vs. Tottenham Hotspur
Dynamo Kiev vs. Club Brugge
Real Sociedad vs. Manchester United
Benfica vs. Arsenal
Red Star Belgrade vs. AC Milan
Royal Antwerp vs. Rangers
Slavia Prague vs. Leicester City
FC Salzburg vs. Villarreal
Braga vs. AS Roma
Krasnodar vs. Dinamo Zagreb
Young Boys vs. Bayer Leverkusen
Molde vs. TSG Hoffenheim
Granada vs. Napoli
Maccabi Tel Aviv vs. Shakhtar Donetsk
Lille vs. Ajax Amsterdam
Olympiakos vs. PSV Eindhoven
Source: espn.co.uk