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Premier League leaders Liverpool will face Sparta Prague in the last 16 of the Europa League, while Brighton face another glamour tie against Roma.
Liverpool will travel to the Czech capital for the first leg on March 7, before a return at Anfield a week later in a competition Liverpool have won three times in the past.
Brighton's maiden European campaign takes them to the Italian capital after they topped Group B containing Marseille, Ajax and AEK Athens.
Europa Conference League holders West Ham face German team Freiburg, while Rangers are up against two-time European champions Benfica from Portugal. David Moyes' side beat Freiburg twice in the group stages:
"I don't think it makes it any easier," the West Ham boss said. "The group was very tight, the games were close, I don't see a huge difference.
"There are some huge teams in the competition - top of the English league, top of the German league - so you want to avoid them, but it is a tough game."
He added: "The manager (Christian Streich) has done a great job at Freiburg, he's had a great length of time at one club. We're looking forward to going back and playing them again.
"I thought they were the toughest team in the group and we've got to try to go back there and win for a second time."
Philippe Clement declared Rangers as underdogs for the first time since he became manager. Benfica sit joint-top of the Portuguese Primeira Liga table with rivals Sporting Lisbon, having played a game more.
Clement, who has dragged Rangers from seven points behind Celtic to two points clear of the Hoops at the top of the Scottish Premiership ahead of the visit of third-placed Hearts on Saturday, surveyed a difficult but winnable European tie.
"It is a really exciting challenge because it is a very good team," said the Belgian boss.
"I think it will be the first game since I have been here that we have been underdogs in a game. That is the reality. I don't see us as underdogs against Celtic. I see us as two teams at a similar level competing and so that is different to Benfica."
Aston Villa will meet Dutch giants Ajax in the last 16 of the Europa Conference League.
The Europa League final will take place in Dublin on May 22, with the Conference League final taking place in Athens a week later.
Liverpool reached the knockout phase of Europe's second-tier competition by topping Group E.
Sparta are the reigning Czech champions and qualified for the knockout round play-off by finishing second in Group C. The clubs met in this competition back in 2011.
Brighton face a Roma side which reached the last 16 with a penalty shoot-out victory over Feyenoord in a play-off on Thursday night. The Giallorossi are in transition following the decision last month to sack Jose Mourinho.
Scottish Premiership Rangers met Benfica in the Europa League group stage in 2020-21.
These games will be played on March 7 and March 14.
Aston Villa were drawn to face Dutch giants Ajax in the last 16 of the Europa Conference League.
Villa progressed as Group E winners and now face the Amsterdam club, who have been champions of Europe four times.
Ajax signed England midfielder Jordan Henderson last month, although he did not feature as they beat Norwegian side Bodo Glimt in extra-time to progress from the knockout play-off round.
The first leg will be played in Amsterdam on March 7, with the return at Villa Park on March 14. The Conference League final takes place in Athens on May 29.
March 7: Europa League and Conference League last-16 first legs
March 14: Europa League and Conference League last-16 second legs
March 15: Europa League and Conference League quarter-final and semi-final draws
April 11: Europa League and Conference League quarter-final first legs
April 18: Europa League and Conference League quarter-final second legs
May 2: Europa League and Conference League semi-final first legs
May 9: Europa League and Conference League semi-final second legs
May 22: Europa League final - Dublin, Ireland
May 29: Europa Conference League final - Athens, Greece
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