Manchester City will take on title holders Real Madrid in a play-off over two legs for a place in the Uefa Champions League last 16.
Friday's draw was for the teams that finished ninth to 24th in the recently concluded Champions League group phase.
City, who won the Champions League for the first time in 2023, will face 15-time record holders Real Madrid over two legs next month.
An all-French affair sees Brest take on Ligue 1 heavyweights Paris Saint-Germain while Celtic take on six-time winners Bayern Munich.
Sporting will meet Borussia Dortmund, Club Brugge take on Atalanta, Monaco meet Benfica, Juventus are paired with PSV while fellow Dutch club Feyenoord also face Italian opposition in AC Milan.
Play-off fixtures
Matches to take place February 11-12 and 18-19 to decide who goes through to the last 16.
Brest v PSG
Celtic v Bayern Munich
Club Brugge v Atalanta
Feyenoord v AC Milan
Juventus v PSV
Manchester City v Real Madrid
Monaco v Benfica
Sporting v Borussia Dortmund
Who meets in the last 16?
Liverpool and Barcelona cannot meet until the final now after finishing first and second.
The Reds will play one of Monaco, Brest, PSG or Benfica in the last 16 – with Barca facing another of those teams.
Arsenal, who finished third, will play Feyenoord, Juventus, AC Milan or PSV.
Aston Villa, who just finished in the top eight after beating Celtic, will take on Sporting, Club Brugge, Atalanta or Borussia Dortmund.
Those ties will take place on March 4-5 and 11-12.
