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European powerhouses are set for intense battles in the UEFA Champions League knockout phase play-offs, with Manchester City drawn against record-holders Real Madrid.
Meanwhile, Celtic face a daunting challenge against Bayern Munich, while Paris Saint-Germain take on Brest in an all-French encounter.
Man City narrowly secured their spot in the top 24 with a crucial 3-1 victory over Club Brugge on the final day of the league phase. However, their lower ranking has set up an early high-stakes clash with Carlo Ancelotti's formidable Madrid side.
Celtic have less than two weeks to devise a strategy to contain Bayern's prolific striker Harry Kane and his attacking teammates, having already conceded seven goals against Bundesliga rivals Borussia Dortmund in October.
Elsewhere, Juventus will go head-to-head with PSV Eindhoven.
Under the new bracket system, each team could only face one of two predetermined opponents based on their final league standings.
As a result, City and Celtic were already aware that either Real Madrid or Bayern Munich awaited them.
Liverpool, Arsenal, and Aston Villa have secured a direct path to the last 16 after finishing in the top eight. They will learn their next opponents in the upcoming draw on February 21.
The first-leg fixtures are scheduled for February 11 and 12, with the return matches set for February 18 and 19.
Full Champions League play-offs draw
Club Brugge v Atalanta
Sporting CP v Borussia Dortmund
Manchester City v Real Madrid
Celtic v Bayern Munich
Juventus v PSV Eindhoven
Feyenoord v AC Milan
Brest v Paris Saint-Germain
Monaco v Benfica