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.
Jump to: Europa League draw reaction
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. The first legs will be on Feb. 18 with returns on Feb. 25
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
Real Sociedad vs. Manchester United
Benfica vs. Arsenal
Red Star Belgrade vs. AC Milan
Royal Antwerp vs. Rangers
Slavia Prague vs. Leicester City
Braga vs. AS Roma
Krasnodar vs. Dinamo Zagreb
Young Boys vs. Bayer Leverkusen
Molde vs. TSG Hoffenheim
Maccabi Tel Aviv vs. Shakhtar Donetsk
Lille vs. Ajax Amsterdam
What to expect (by Mark Ogden)
The knockout stages of the Europa League promise to be tougher than ever with the draw for the round of 32 including the leaders of the English, French, Spanish, German and Italian leagues.
With the competition winners earning direct qualification for next season's Champions League, the race to the final in Gdansk will be intense with such a huge prize at stake. And the biggest clubs in the Europa League had mixed fortunes when the draw for the round of 32 was made on Monday.
Wolfsberger AC vs. Tottenham
Having already beaten Austrian league high-flyers LASK Linz in the group stage, Spurs should have no concerns against Austrian side Wolfsberger AC, who are mid-table and out of the European places in their domestic competition.
Midfielder Michael Liendl, with four goals in five group games, will be the biggest threat against Spurs, but Jose Mourinho will be able to rest his star players for this tie and still confidently expect to go through.
Who qualifies?: Spurs
Real Sociedad vs. Manchester United
The tie of the round, but also the worst possible draw for two clubs with genuine ambitions of winning the Europa League this season.
La Real are the surprise leaders of La Liga, with former Manchester City midfielder David Silva inspiring the team to the top of the table. Former United midfielder Adnan Januzaj is another player for Ole Gunnar Solskjaer's team to watch.
Having dropped into the Europa League from the Champions League, United would have hoped for a much easier tie and they will need to be at their best to make it through this one.
Who qualifies?: Manchester United
Benfica vs. Arsenal
A Champions League fixture being played out in the Europa League -- that is the harsh reality for these two great clubs ahead of their round-of-32 encounter.
Benfica are second in Portugal right now, while Arsenal are in the bottom sixth after their worst-ever start to a Premier League season. But by the time the game comes around in February, Arsenal will surely have emerged from their slump. Won't they?
Who qualifies?: Arsenal
Red Star Belgrade vs. AC Milan
A throwback clash between two European Cup winners from the 1990s, but one which sees the unbeaten leaders of the Serbian SuperLiga take on the unbeaten leaders of Italy's Serie A.
Red Star will be a tough opponent for Milan, but with Zlatan Ibrahimovic still going strong at 39, the Italian giants should be favourites to go through.
Who qualifies?: AC Milan
Royal Antwerp vs. Rangers
Steven Gerrard's Rangers are unbeaten in all competitions this season and on course to win the Scottish title for the first time since 2011, but their progress in Europe has been an unexpected bonus for the former Liverpool captain.
Rangers will expect to win this tie and make it to the round of 16 where they could secure a 'Battle of Britain' clash against one of the four remaining Premier League teams.
Who qualifies?: Rangers
Slavia Prague vs. Leicester
This looks a comfortable tie for Leicester, but Czech champions Slavia have an emerging team of homegrown players who were able to beat German Bundesliga leaders Bayer Leverkusen in the group stage, as well as record home and away wins against Nice.
Brendan Rodgers has a team more than capable of progressing, but Slavia are dangerous and Leicester will pay the price for any complacency.
Who qualifies?: Leicester