Manchester United will face Paris Saint-Germain in the Champions League round of 16, while Liverpool have been drawn against Bayern Munich.
Atletico Madrid take on Juventus, Tottenham Hotspur are up against Borussia Dortmund, and Real Madrid face Ajax.
Barcelona play Lyon, Manchester City meet Schalke, while AS Roma vs. Porto completes the round of 16 ties.
PSG, who finished ahead of Liverpool and Napoli to top Group C, are undefeated in Ligue 1 this season and will travel to Old Trafford before hosting United in Paris.
United are struggling in the Premier League and fell 19 points behind leaders Liverpool following their 3-1 defeat at Anfield on Sunday, although PSG manager Thomas Tuchel said it remains a challenging fixture.
“It’s always difficult,” Tuchel said after Monday’s draw. “Manchester United has a lot of experience in this competition. It’s still really hard to play at Old Trafford.
“The favourite PSG? No, I do not think so. At PSG, we lack experience in the quarter, half and final.
Manchester United has a lot of experience. We are able to win, but it is a big challenge.”
Bayern Munich and Liverpool, who are both five-time winners of the competition, will meet in a competitive game for the first time since 2001, while Spurs face Dortmund and City play Schalke in the other clashes between English and German opposition.
Liverpool manager Jurgen Klopp is familiar with Bayern, having spent his entire managerial career in Germany before moving to Anfield. Klopp also lost to Bayern in the 2013 Champions League final while with Dortmund and said he is prepared for a “difficult” tie.
“It was clear it would be difficult; they are obviously a top side,” Klopp said. “For me, it’s nice, going to Germany. But it’s just the draw. So we have now time to prepare the game, a lot of time obviously, and hopefully we have all our players available then. It will be a tough one, an interesting one, and I am looking forward to it.
“In the last couple of years, they have dominated the German league in the best period of German football. Everybody was talking about Germany being in a really good moment and Bayern was dominating the league, that’s the truth. It’s obviously long ago that I played Bayern in a competitive game, so I’m really looking forward to it.”
Support InfoStride News' Credible Journalism: Only credible journalism can guarantee a fair, accountable and transparent society, including democracy and government. It involves a lot of efforts and money. We need your support. Click here to Donate