Arsenal will play Porto in the UEFA Champions League last 16, while title holders Manchester City take on Copenhagen.
City won the treble last season under Pep Guardiola when they defeated Inter Milan in the final, completing a clean sweep of the major trophies available to the team.
While they have not reached the heights they did last season in the Premier League, in part due to an injury to Kevin De Bruyne, they topped Group G by winning every single one of their six matches in Europe.
The draw is one that City will be heavy favourites to negotiate regardless of any injury concerns, while they are also unsure when they can recall Erling Haaland, who is a doubt for them in the upcoming Club World Cup.
FC Porto, winners in 2004 under Jose Mourinho, were drawn against Arsenal, who continue to impress under Mikel Arteta and are attempting to compete on two fronts.
Arsenal are the only other Premier League side to reach the Champions League knockout rounds after Manchester United and Newcastle United were both eliminated in the group stages.
Italian champions Napoli, who have struggled in Serie A since the departure of Luciano Spalletti in the summer, were drawn against FC Barcelona.
While Barcelona won La Liga last season under former club captain Xavi Hernandez, they have failed to find their feet this campaign and sit in third place in the league table, seven points off the top.
Barcelona are set to contest the four-team Spanish Super Cup in Saudi Arabia in January before European tournaments restart.
The first legs will take place across February 13-14 and 20-21 next year, with the return matches across March 5-6 and 12-13.
CHAMPIONS LEAGUE LAST 16 DRAW
- Porto v Arsenal
- Napoli v Barcelona
- PSG v Real Sociedad
- Internazionale v Atletico Madrid
- PSV Eindhoven v Borussia Dortmund
- Lazio v Bayern Munich
- Copenhagen v Manchester City
- RB Leipzig v Real Madrid
