Manchester United have been drawn against La Liga leaders Real Sociedad in the last 32 of the Europa League, while Arsenal take on Benfica.
Tottenham will face Austrian side Wolfsberger and Leicester meet Slavia Prague.
Steven Gerrard’s Rangers, who are unbeaten this season, have been paired with Belgium side Royal Antwerp.
The round of 32 ties will take place on February 18 (first leg) and 25 (second leg) followed by the last 16 ties on March 11 and 18. Tottenham’s home second leg will be on Wednesday, February 17 to avoid a clash with Arsenal’s home tie against Benfica on Thursday, February 18.
Manchester United appear to have the toughest draw among the five British teams as they face Sociedad, who have only lost once in La Liga and finished behind Napoli in their Europa League group.
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Benfica, who are second in the Portuguese league, look like a tricky test for Arsenal too, but Spurs will start as strong favourites against Wolfsberger, who are eighth in the Austrian top-flight.
Leicester and Rangers will also be fancied to advance to the last 16.
EUROPA LEAGUE LAST 32 DRAW
- Wolfsberger vs Tottenham
- 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
- Salzburg vs Villarreal
- Braga vs Roma
- Krasnador vs Dinamo
- Young Boys vs Bayer Leverkusen
- Molde vs Hoffenheim
- Granada vs Napoli
- Maccabi Tel-Aviv vs Shakhtar Donetsk
- Lille vs Ajax
- Olympiacos vs PSV Eindhoven