Jose Mourinho’s AS Roma will play Feyenoord in the knockout round play-offs of the UEFA Europa League.
Mourinho is the only manager to have won all three of the current European trophies, having also won the Europa Conference League with Roma, and the Champions League with Inter Milan and Porto.
The Portuguese manager also claimed the Europa League trophy in his first season with Manchester United in 2017.
Roma are currently seventh in Serie A while Feyenoord, who sit 10 points off the top league leaders PSV, are second in the Eredivisie.
Mourinho’s first club as manager, Benfica, will play Ligue 1 side Toulouse, while another Primeira Liga side, Braga, face a daunting trip to Azerbaijan to meet Qarabag.
The second Lisbon side in the draw, Sporting Club, face Swiss stalwarts Young Boys.
RC Lens, who were knocked out of the Champions League group stage, take on Bundesliga outfit Freiburg, while French outfit Stade Rennais take on Italian giants AC Milan.
Galatasaray, due to play the Turkish Super Cup in Saudi Arabia later this month against Intercontinental rivals Fenerbahce, will play Czech side Sparta Prague.
Shakhtar Donetsk, who are obliged to play their home fixtures outside of Ukraine due to the invasion by Russia, will take on Olympique Marseille.
British sides Brighton, Liverpool, Rangers and West Ham are all through to the last 16. They will find out their opponents in the next draw on February 23.
In the Europa Conference League, Aston Villa, Club Bruges, Fenerbahce, Fiorentina, Lille, Maccabi Tel Aviv, PAOK, Viktoria Plzen are also waiting for February 23 to find out their last-16 fixtures.
The pick of the Round of 16 include Ajax v Bodo/Glimt, Real Betis v Dinamo Zagreb, and Union Saint-Gilloise against last year’s beaten finalists, Eintracht Frankfurt.
The first legs for both tournaments will take place across February 15 next year, with the return matches on February 22.
EUROPA LEAGUE KNOCKOUT ROUND PLAY-OFF DRAW
- Feyenoord v Roma
- AC Milan v Rennes
- Lens v Freiburg
- Young Boys v Sporting Lisbon
- Benfica v Toulouse
- Braga v Qarabag
- Galatasaray v Sparta Prague
- Shakhtar Donetsk v Marseille
