Trent Alexander-Arnold could face a frosty reception at Anfield after the Champions League draw threw up a fascinating reunion.
Alexander-Arnold is set to return to boyhood club Liverpool after he left earlier this summer, initially agreeing a free transfer before Real Madrid paid a fee of £8.5million ($11.5m) to accelerate the move ahead of the Club World Cup.
Many Liverpool fans were left upset that the 26-year-old allowed his contract to run down, and he was booed by some during his final few appearances for the club with which he won two Premier League titles, the Champions League, FA Cup and League Cup among other honours.
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The England international has had a difficult start to life in Spain as he battles Dani Carvajal for a place in the side coached by former Liverpool midfielder Xabi Alonso.
The Premier League champions will host Madrid and Atlético Madrid at home, while they will visit the San Siro to take on Inter Milan.
Anfield will also play host to matches against PSV Eindhoven and Qarabag with away trips to Frankfurt, Marseille, and Galatasaray coming up for Arne Slot's side.