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Three-time winners Liverpool were drawn to face Sparta Prague in the Europa League last 16 on Friday, while unbeaten Bundesliga leaders Bayer Leverkusen will take on Azeris Qarabag.
Jurgen Klopp's Liverpool will be strong favourites to reach the quarter-finals as they bid for a quadruple in the German's final season before stepping down as manager.
The first leg will be played in the Czech capital on 7 March, with Anfield hosting the return game a week later.
Leverkusen, led by Xabi Alonso, are unbeaten in 32 matches in all competitions this season, and will again face Qarabag, having already seen off the Azeri champions twice in the group stage.
Also renewing acquaintances will be last year's Europa Conference League winners West Ham and Freiburg, after David Moyes' side's brace of victories against the Bundesliga club in Group A.
Seven-time European champions AC Milan continue their bid to win a maiden Europa League title against Slavia Prague after their knock-out round play-off win over Rennes.
Scottish Premiership leaders Rangers, losing finalists in 2022, take on Portuguese Primeira Liga pace-setters Benfica, still chasing a first European trophy since 1962.
Premier League club Brighton continue their first ever European adventure at last season's runners-up Roma.
Europa League last-16 draw:
Sparta Prague (CZE) v Liverpool (ENG)
Marseille (FRA) v Villarreal (ESP)
Roma (ITA) v Brighton (ENG)
Benfica (POR) v Rangers (SCO)
Freiburg (GER) v West Ham (ENG)
Sporting Lisbon (POR) v Atalanta (ITA)
AC Milan (ITA) v Slavia Prague (CZE)
Qarabag (AZE) v Bayer Leverkusen (GER)
- First legs to be played on 7 March, second legs to be played on 14 March
Ajax drawn against Aston Villa in Conference League
Meanwhile, four-time European champions Ajax were drawn to face Premier League club Aston Villa in the Europa Conference League last 16 next month.
Ajax, who edged out Bodo/Glimt in extra time in the knock-out play-off round on Thursday, will host the first leg in Amsterdam on March 7 before the return game in Birmingham seven days later.
Aston Villa, the 1982 European champions, are playing in continental competition for the first time since 2010 this season and sit fourth in the Premier League.
Their manager Unai Emery has won the Europa League four times as a head coach.
Europa Conference League last-16 ties after Friday's draw:
Servette (SUI) v Viktoria Plzen (CZE)
Ajax (NED) v Aston Villa (ENG)
Molde (NOR) v Club Brugge (BEL)
Union Saint-Gilloise (BEL) v Fenerbahce (TUR)
Dinamo Zagreb (CRO) v PAOK (GRE)
Sturm Graz (AUT) v Lille (FRA)
Maccabi Haifa (ISR) v Fiorentina (ITA)
Olympiakos (GRE) v Maccabi Tel Aviv (ISR)
- First legs to be played on 7 March, second legs to be played on 14 March
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