Real Madrid and Liverpool will contest a repeat of last season's Champions League final during the round of 16 following Monday's draw.
Madrid reached the knockout stages as Group F winners, an outcome they will have been hoping would secure them a favourable tie.
But by being paired with Liverpool, Carlo Ancelotti's men were given arguably the hardest draw possible in what will be a repeat of the 2021-22 and 2017-18 finals.
There will also be a replay of the 2019-20 showpiece between Bayern Munich and Paris Saint-Germain.
Die Roten prevented PSG from winning their first continental crown that year, with revenge on the cards for the Parisians early next year.
Chelsea, winners most recently in 2021, will go up against the youthful Borussia Dortmund, while Manchester City – beaten finalists last year – are also due to tussle with Bundesliga opposition in RB Leipzig.
Antonio Conte faces a return to his homeland and San Siro as Tottenham prepare to duel with Italian champions Milan, while Serie A leaders Napoli – who won their group ahead of Liverpool – will fancy their chances against Europa League holders Eintracht Frankfurt.
The first legs will take place across the weeks commencing February 13 and 20, with the return fixtures scheduled for the weeks commencing March 6 and 13.
Last-16 draw in full:
RB Leipzig v Manchester City
Club Brugge v Benfica
Liverpool v Real Madrid
Milan v Tottenham
Eintracht Frankfurt v Napoli
Borussia Dortmund v Chelsea
Inter v Porto
Paris Saint-Germain v Bayern Munich