Liverpool have been drawn against German champions Bayern Munich in the Champions League round of 16.
Tottenham and Manchester City will also face German opposition in Borussia Dortmund and Schalke 04 respectively, while Manchester United were drawn against French champions PSG.
Following a 3-1 Premier League defeat at Liverpool on Sunday, being paired against the runaway Ligue 1 leaders, who scored 17 goals in their Group C campaign to qualify ahead of the Reds, was perhaps not the most kindest draw which United boss Jose Mourinho would have been hoping for.
It is, though, the first time the Red Devils will have played Paris St-Germain.
Elsewhere in Monday's draw, Atletico Madrid will take on Serie A leaders Juventus, Lyon play Barcelona, Roma face Porto while Dutch club Ajax are set to meet holders Real Madrid.
Bayern Munich defender Mats Hummels, who played under Liverpool manager Jurgen Klopp at Borussia Dortmund, has tweeted his reaction to Bayern drawing the Reds in the last 16.
I 👀 u my former coach 😁— Mats Hummels (@matshummels) December 17, 2018
The first leg fixtures will be split over two midweek dates, on February 12/13 and 19/20, with the second legs played over March 5/6 and 12/13.
Schalke 04 (GER) v Manchester City (ENG)
Atlético Madrid (ESP) v Juventus (ITA)
Manchester United (ENG) v Paris St-Germain (FRA)
Tottenham Hotspur (ENG) v Borussia Dortmund (GER)
Lyon (FRA) v Barcelona (ESP)
Roma (ITA) v Porto (POR)
Ajax (NED) v Real Madrid (ESP)
Liverpool (ENG) v Bayern (GER)