Chelsea will face Champions League holders Real Madrid in the quarter-finals, as Manchester City clash with Pep Guardiola’s former side Bayern Munich.
Both Premier League sides will 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.
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.
Meanwhile, 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.
Pep Guardiola managed Bayern Munich between 2013 and 2016
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.
Chelsea have only lost one of their seven games against Real Madrid in European competition – indeed, they have the lowest percentage of losses against Real Madrid (14%) of any side to have played them 5+ times in Europe.
Chelsea’s only defeat in seven matches against Real Madrid in Europe came in their most recent one at Stamford Bridge, losing 1-3 in the 2021-22 quarter-final first leg.
Real Madrid have won their last four UEFA Champions League ties against English sides, beating Chelsea in last season’s quarter-final, Manchester City in last season’s semi-finals and Liverpool in last season’s final and this season’s round of 16.
All six previous meetings between Man City and Bayern Munich came in the UEFA Champions League group stages (2011-12, 2013-14, 2014-15), with each side winning three times.
This will be Pep Guardiola’s first meeting with Bayern Munich since leaving the club. His only managerial games against them came in the 2008-09 Champions League quarter-finals, knocking them out with Barcelona en route to lifting the trophy.
Man City have progressed from all four of their previous UEFA Champions League knockout ties against German clubs, including one quarter-final (2020-21 v Borussia Dortmund).