Pep Guardiola’s Manchester City will face Real Madrid in the last 16 of the Champions League while holders Liverpool go up against Atletico Madrid.
For Liverpool, it will mean a return to Atletico’s Wanda Metropolitano stadium where they lifted last season’s Champions League title in May.
Elsewhere, Tottenham will face tough opposition in the shape of Bundesliga leaders, RB Leipzig.
Chelsea, meanwhile, have been drawn against Bayern Munich in a repeat of the 2012 final won by the London club.
Other stand out fixtures from Monday’s draw include Borussia Dortmund’s tie against French champions Paris Saint Germain which will see their coach, Thomas Tuchel, return to the Westfalenstadion.
Lionel Messi’s Barcelona will face Italian side Napoli while Lyon will hope to upset Cristiano Ronaldo’s Juventus.
Atalanta, which has reached the last 16 in its debut Champions League season, will play Spanish side Valencia.
Borussia Dortmund v PSG
Real Madrid v Manchester City
Atalanta v Valencia
Atletico Madrid v Liverpool
Chelsea v Bayern Munich
Lyon v Juventus
Tottenham v RB Leipzig
Napoli v Barcelona