Manchester United midfielder Paul Pogba could face his brother Florentin after Jose Mourinho’s side were drawn against St Etienne in the Europa League round of 32.
Florentin Pogba, a Guinean international, is a defender for St Etienne although he has only been picked intermittently this season. His brother Paul, who plays for France, joined United from Juventus in the close season for a world record fee.
Tottenham were handed the short trip to Belgium to face Group H runners-up Gent, who qualified by winning their final match against Konyaspor.
Borussia Moenchengladbach and Fiorentina, two of the most familiar names in European club football, will meet for the first time.
AS Roma, the only other Serie A team left in the competition after Inter Milan and Sassuolo failed to get past the group stage, are involved in another high-profile match against Spain’s Villarreal.
Israel’s Hapoel Beer Sheva, who beat Inter during the group stage, were rewarded with a tie against Besiktas, one of eight teams parachuting in from the Champions League.
Two of the other top ties pitted AZ Alkmaar against Olympique Lyonnais and PAOK against Schalke, a repeat of their Champions League playoff tie in 2013-14 which the Bundesliga side edged 4-3 on aggregate.
UEFA Europa League Round of 32:
Athletic Bilbao v Apoel Nicosia
Legia Warsaw v Ajax
Anderlecht v Zenit St Petersburg
FC Astra Giurgiu v Genk
Man Utd v St Etienne
Villarreal v Roma
Ludogorets v FC Copenhagen
Celta Vigo v Shakhtar Donetsk
Olympiacos v Osmanlispor
AA Gent v Tottenham
Rostov v Sparta Prague
Krasnodar v Fenerbahce
Borussia M’gladbach v Fiorentina
AZ v Lyon
Hapoel Beer Sheva v Besiktas
PAOK Salonika v Schalke 04