Manchester United have been drawn against LaLiga outfit Real Sociedad in the Europa League round of 32.
United were dumped out of the Champions League after losing to RB Leipzig on matchday six, despite topping their group going into the contest in Germany.
Sociedad, meanwhile, finished second to Napoli in Europa League Group F, although they are enjoying a great domestic season and sit top of LaLiga after 13 games.
Arsenal, who are struggling in the Premier League despite a maximum 18-point return in the group stage, face a tough test against Portuguese side Benfica. They are second in the Primeira Liga after nine games.
Tottenham have been drawn against Austrian side Wolfsberger, who finished second in Group K. Jose Mourinho's side beat Royal Antwerp on matchday six to top Group J.
Antwerp will face another British side in Rangers, who topped Group D with four wins and two draws. Leicester's reward for finishing top of Group G is a tie against Slavia Prague.
Europa League round of 32 draw
- Wolfsberger v Tottenham
- Dynamo Kyiv v Club Brugge
- Real Sociedad v Manchester United
- Benfica v Arsenal
- Crvena Zvezda v AC Milan
- Royal Antwerp v Rangers
- Slavia Prague v Leicester
- Salzburg v Villarreal
- Braga v 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
- Olympiacos v PSV Eindhoven