Holders Chelsea will play Real Madrid in the Champions League quarter-finals and could meet Manchester City in the last four of the competition.
City were paired with Atletico Madrid – round of 16 conquerors of Manchester United on Tuesday – while Liverpool were drawn against Benfica.
Villarreal will play Bayern Munich in the remaining quarter-final.
The draw made at UEFA headquarters in Nyon means Chelsea, who beat City in the final last May to win the trophy for the second time, will have a last-eight reunion with former manager Carlo Ancelotti.
Chelsea were drawn to play the first leg at Stamford Bridge but the tie is set to be reversed.
The two Madrid teams cannot be at home in the same leg and, as Atletico qualified as Spanish champions their tie is set to remain as drawn.
The draw for the semi-final was also conducted in Nyon, throwing up possibilities of a repeat of last season’s clash between Chelsea and Manchester City and an all-Madrid affair.
Chelsea beat City 1-0 in the 2021 final at Porto’s Estadio do Dragao with Kai Havertz scoring the winner.
Benfica or Liverpool – who knocked out Inter Milan 2-1 on aggregate in the round of 16 – will play Villarreal or Bayern in the other semi-final.
The quarter-final ties will take place on April 5-6 and 12-13, with the semi-finals scheduled for April 26-27 and May 3-4.
The Stade de France in Paris will host the final on May 28 after the game was moved from St Petersburg following Russia’s invasion of Ukraine.
