Manchester City will face Real Madrid while holders Liverpool have been drawn against Atletico Madrid in the last 16 of the Champions League.
Chelsea play Bayern Munich in a repeat of the 2012 final while Tottenham take on another German side, RB Leipzig.
In the pick of the other ties, Borussia Dortmund will play Paris St-Germain and Napoli take on Barcelona.
The first legs will be played on 18, 19, 25 and 26 February with the return matches on 10, 11, 17 and 18 March.
This season’s final is on 30 May at the Ataturk Stadium in Istanbul, the ground where Liverpool won the epic 2005 final against AC Milan when they came back from three down to draw 3-3 and win on penalties.
The Reds’ last-16 draw will take them to Atletico’s Wanda Metropolitano, which also has good memories for Liverpool as it is the stadium in which they won last year’s final.
City’s tie with Real features the first competitive meeting between multiple Champions League-winning managers Pep Guardiola and Zinedine Zidane.
The Frenchman won the competition three times in a row with Los Blancos from 2016 while Guardiola claimed it with Barcelona in 2009 and 2011.
That was Guardiola’s last triumph in the competition though, and his City side were beaten by eventual runners-up Tottenham in the quarter-finals last season.
Spurs have changed manager since then, with Mauricio Pochettino succeeded by Jose Mourinho, who has two previous Champions League wins to his name – Porto in 2004 and Inter Milan in 2010.
Their opponents RB Leipzig currently lead the German Bundesliga and have in Timo Werner one of Europe’s most coveted strikers and in Julian Nagelsmann one of the continent’s most promising young coaches.
Chelsea face a tough tie against five-time Champions League winners Bayern Munich, who are reigning Bundesliga champions but sit fifth in the league and sacked manager Niko Kovac last month.
The other two last-16 ties see Italian club Atalanta, who reached the last 16 despite losing their first three group games, face Valencia of Spain, while Serie A champions Juventus – with Cristiano Ronaldo still in prolific form – take on resurgent French side Lyon.
‘Tough draws for the English sides’
BBC Sport chief football writer Phil McNulty:
The Premier League’s four contenders have all been handed tough Champions League draws that would comfortably grace even later stages in the competition.
Holders Liverpool and Premier League champions Manchester City have both been handed challenging assignments in Madrid.
Atletico Madrid, under the iron rule of Diego Simeone, know how to navigate their way through the Champions League and any trip to the Wanda Metropolitano has its hazards.
Liverpool will still be confident though, as will Manchester City despite drawing Real Madrid in a match that sends coach Pep Guardiola back to the Bernabeu, where he enjoyed success in this competition before with Barcelona.
Chelsea also go to familiar and successful territory after drawing Bayern Munich, who they beat to win the Champions League in 2012.
But while this is also a difficult draw for Frank Lampard’s emerging Chelsea, Bayern are perhaps not the force they were so the Blues manager will feel optimistic.
Spurs boss Jose Mourinho may feel happiest with his draw but the man who has won the trophy twice with Porto and Inter Milan will know RB Leipzig cannot be underestimated under one of Europe’s finest young coaches Julian Nagelsmann.
Last-16 draw in full
Borussia Dortmund v Paris St-Germain
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
Champions League calendar
Last-16 first legs
18 February: Borussia Dortmund v Paris Saint-Germain, Atletico Madrid v Liverpool
19 February: Atalanta v Valencia, Tottenham v RB Leipzig
25 February: Chelsea v Bayern Munich, Napoli v Barcelona
26 February: Real Madrid v Manchester City, Lyon v Juventus
Last-16 second legs
10 March: Valencia v Atalanta, RB Leipzig v Tottenham
11 March: Paris Saint-Germain v Borussia Dortmund, Liverpool v Atletico Madrid
17 March: Manchester City v Real Madrid, Juventus v Lyon
18 March: Bayern Munich v Chelsea, Barcelona v Napoli