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Graham Potter’s Chelsea have been paired with Champions League holders Real Madrid in the quarter-finals draw while Pep Guardiola faces a reunion with former club Bayern Munich.
The matches are likely to be a swim or drown duet with both Premier League sides expected to meet each other in the semi-final, should both Chelsea and City advance through their last-eight ties.
Meanwhile, there will be an all-Italian derby in the quarter-finals as Serie A champions AC Milan face current leaders Napoli, while Inter Milan will take on Benfica.
The first legs of the quarter-finals will take place on April 11 and 12, with the return fixtures on April 18 and 19 and the semi-final first-legs are due to happen on May 9 and May 10, with the return legs on May 16 and May 17.
Chelsea beat Borussia Dortmund 2-1 on aggregate in their last-16 tie, but now face a major task to reach the last four against holders Real.
The Blues exited last season’s Champions League to Real at the same stage – losing the first-leg 3-1 at Stamford Bridge before putting in a valiant outing at the Santiago Bernabeu,
Chelsea, then managed by Thomas Tuchel, went 3-0 up to lead the tie but goals from Rodrygo and Karim Benzema – the latter strike coming in extra-time – saw the Blues crash out 5-4 on aggregate.
Concurrently, Man City manager Guardiola will face a familiar foe in former side Bayern – the club he won seven major titles with between 2013 and 2016, including three Bundesliga titles.
City and Bayern also have a connection through Joao Cancelo, who will be able to play against his parent club after moving on loan to the German side, with an option to make the deal permanent for around £60m.
Should Chelsea and City go on to meet each other in the Champions League last four, it will lead to six meetings between the two clubs in this season alone.
Both Premier League clubs were paired against each other in the third rounds of the FA Cup and Carabao Cup earlier this season.
