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Manchester City will play 15-time European Cup winners Real Madrid and Celtic will face Bayern Munich in the Champions League play-off round.
City, the 2023 Champions League winners, will host Madrid at Etihad Stadium on 11 or 12 February before travelling to Spain for the second leg the following week.
Celtic, winners in 1967, will face Bayern Munich at Celtic Park before the Bundesliga club host Brendan Rodgers' side at Allianz Arena in the second leg.
Brest v Paris St-Germain
Club Brugge v Atalanta
Manchester City v Real Madrid
Juventus v PSV Eindhoven
Monaco v Benfica
Sporting v Borussia Dortmund
Celtic v Bayern Munich
Feyenoord v AC Milan
Clubs that finished in the top eight of the 36-team Champions League group table progressed directly to the last 16. The teams in the bottom eight were eliminated.
The remaining 16 teams that finished between ninth and 24th place progressed into the play-offs.
Of those 16 teams, the clubs that finished ninth to 16th in the league phase were seeded into four pairs for the play-off draw.
Those that finished from 17th to 24th were put into four unseeded pairs.
Unseeded teams were drawn against one of two seeded teams, with seeded teams hosting the second leg of the play-off as they finished higher in the first phase table.
City finished 22nd in the league table while Celtic finished 21st.
It meant the two sides would face one of Real Madrid or Bayern Munich, who finished 11th and 12th respectively in the group stage.