Three-times European champions Manchester United face Danish champions Midtjylland in the last 32 of the Europa League after failing to qualify for the Champions League knockout phase.
United were one of three English sides in Monday's draw in Nyon, with Liverpool boss Jurgen Klopp set to return to Germany as the Reds were drawn against European newcomers Augsburg.
Tottenham Hotspur were handed a testing two-legged tie against Serie A title hopefuls Fiorentina, having crashed out at the hands of the Italians at the same stage in last season's competition.
United slumped to a 3-2 defeat at Wolfsburg last week in the final round of Champions League group games, condemning Louis van Gaal's side to a third-place finish in Group B and they are without a win in five matches in all competitions.
However, the Red Devils will be overwhelming favourites to advance against a Midtjylland side that reached the knockout stages despite suffering two heavy defeats against Napoli during the group phase.
"Miracles have happened before, and we will probably need one again," said Midtjylland coach Jess Thorup, whose side have already claimed one Premier League scalp after knocking out Southampton in the final qualifying round.
Goalkeeper Mikkel Andersen was delighted after being paired with the three-time European champions, saying: "This is as big as it gets."
Liverpool will also be expected to see off an Augsburg side that had spent much of this season's Bundesliga campaign in the relegation zone before Sunday's 2-1 win over Schalke.
But Augsburg coach Markus Weinzierl was thrilled with the outcome of the draw, regardless of the task that awaits his players.
"We are happy about this draw. This game is something special. Liverpool are a cult, Jurgen Klopp is a huge name in Germany too," said Weinzierl.
"Klopp knows us and will not underestimate us. We will be outsiders against Liverpool, but are gladly accepting that role."
Defending champions Sevilla, who followed United out of the Champions League, will begin their quest for a third straight Europa League title against Ole Gunnar Solskjaer's Molde, while Borussia Dortmund take on Porto.
Other notable ties include Gary Neville's Valencia facing Rapid Vienna, Sporting Lisbon against Bayer Leverkusen and Villarreal versus Napoli.
The first legs will be played on February 18 with the return matches scheduled to take place a week later.
Source: AFP
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