Premier League leaders Liverpool have been handed a Champions League last-16 tie against German giants Bayern Munich.
In the first fixture drawn in Nyon on Monday morning, Premier League champions Manchester City were paired against German club Schalke.
Manchester United were handed a tough tie against French champions Paris St Germain.
Tottenham Hotspur, who qualified as runners-up in their group behind Barcelona, will also face Bundesliga opposition as they face Borussia Dortmund.
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.
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.
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.
The 30-year-old posted: "I (eyes emoji) ?? u my former coach" followed by a grinning emoji.
The teams will meet for the first leg in February.
PSG coach Thomas Tuchel has confidence in his Ligue 1 leaders, but warned against complacency.
"We have the quality to win at Old Trafford. I'm confident for my team, but it's a great test, a challenge," Tuchel said at a press conference ahead of the Ligue 1 game against Orleans.
"The round of 16 is always tough. Manchester United have a lot of experience in this competition, which they've won several times.
"I'm neither satisfied nor unsatisfied by the draw."
More to follow