Swansea have been drawn against Napoli in what appears a cracking tie as reward for their advancement from the group stages.
Tottenham, the only other Premier League side remaining in the competition, will play Ukrainian side Dnipro Dnipropetrovsk.
With the club managerless following the sacking of Andre Villas-Boas this morning, it will be seen as an irony that they will come up against a team managed by Juande Ramos, who was dismissed from White Hart Lane in 2008.
While Swansea's tie will be seen as the more glamourous, it will be much tougher to negotiate. Napoli, managed by former Liverpool and Chelsea boss Rafael Benitez, may have dropped out of the Champions League, but only on goal difference in a particularly tough group that included Borussia Dortmund and Arsenal.
Should Spurs come through the two-legged tie against Dnipro, they face a last 16 encounter against the winner of PAOK v Benfica, with the latter finishing as last season's runners-up after they lost the final to Chelsea.
For Swansea, should they record what would be a historic and shock win over Napoli, they would face another extremely testing two-legged affair against the winner of Porto v Frankfurt.
Europa League Round of 32 (to be played on February 20 and 27):
FC Dnipro Dnipropetrovsk v Tottenham Hotspur FC
Real Betis Balompié v FC Rubin Kazan
Swansea City AFC v SSC Napoli
Juventus v Trabzonspor AŞ
NK Maribor v Sevilla FC
FC Viktoria Plzeň v FC Shakhtar Donetsk
FC Chornomorets Odesa v Olympique Lyonnais
SS Lazio v PFC Ludogorets Razgrad
Esbjerg fB v ACF Fiorentina
AFC Ajax v FC Salzburg
Maccabi Tel-Aviv FC v FC Basel 1893
FC Porto v Eintracht Frankfurt
FC Anji Makhachkala v KRC Genk
FC Dynamo Kyiv v Valencia CF
PAOK FC v SL Benfica
FC Slovan Liberec v AZ Alkmaar
Europa League Round of 16 draw (to be played on March 13 and 20):
Slovan Liberec/AZ Alkmaar v Anzhi/Racing Genk
Lazio/Ludogorets Razgrad v Dynamo Kiev/Valencia
Porto/Eintracht Frankfurt v Swansea City vs. Napoli
Chornomorets/Lyon v Viktoria Plzen/Shakhtar Donetsk
Maribor/Sevilla v Real Betis/Rubin Kazan
Dnipro/Tottenham v PAOK/Benfica
Maccabi Tel-Aviv/Basel v Ajax/Red Bull Salzburg
Juventus/Trabzonspor v Esbjerg/Fiorentina