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.
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