Manchester United will face Danish side Midtjylland in the last 32 of the Europa League after failing to make the knockout stage of the Champions League.
United were beaten 3-2 by Wolfsburg in the final set of group games last week and now face the side that put Southampton out of the competition during the qualifying stage.
Tottenham's reward for winning their group is a tough trip to Italy to take on Serie A side Fiorentina, who knocked Mauricio Pochettino's side out 3-1 on aggregate at the same stage last season.
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And there will be a return to Germany for Liverpool boss Jurgen Klopp, although not against his former club Borussia Dortmund, who were a possible opponent.
They will instead take on Augsburg, who only qualified for the last 32 with a late goal in their final group match against Partizan Belgrade.
Defending champions Sevilla take on Norwegian side Molde and Gary Neville's Valencia will face Austrian opposition in Rapid Vienna.
Round of 32 draw:
Valencia v Rapid Vienna
Fiorentina v Tottenham
Borussia Dortmund v Porto
Fenerbahce v Lokomotiv Moscow
Anderlecht v Olympiakos
Midtjylland v Manchester United
Augsburg v Liverpool
Sparta Prague v Krasnodar
Galatasaray v Lazio
Sion v Braga
Shakhtar Donetsk v Schalke 04
Marseille v Athletic Bilbao
Sevilla v Molde
Sporting Lisbon v Bayer Leverkusen
Villarreal v Napoli
Saint-Etienne v Basel