Managerless Tottenham will come up against former boss Juande Ramos after being drawn to face Ukrainian outfit Dnipro in the last 32 of the Europa League, while Swansea have been tasked with overcoming Serie A title hopefuls Napoli.
Ramos was in charge of Spurs for just under a year from October 27, 2007 before being sacked with the club bottom of the Premier League in the 2008-09 season having taken just two points from their opening eight matches.
He will therefore be intent on gaining a measure of revenge over his former side, who announced the sacking of Andre Villas-Boas on Monday morning, despite the Portuguese overseeing a 100 per cent record in Europe this season.
Swansea, meanwhile, will face Napoli, who finished third in Arsenal’s Champions League group.
Full Europa League last 32 draw…
Dnipro v Spurs
Real Betis v Rubin Kazan
Swansea v Napoli
Juventus v Trabzonspor
Maribor v Sevilla
Viktoria Plzen v Shakhtar Donetsk
Chornomorets v Lyon
Lazio v Ludogorets
Esbjerg v Fiorentina
Ajax v RB Salzburg
Maccabi Tel-Aviv v Basel
FC Porto v Eintracht Frankfurt
Anzhi Makhachkala v Genk
Dynamo Kiev v Valencia
PAOK v Benfica
Slovan Liberec v AZ
First legs to be played 20th February, 2014; Second legs to be played 27th February, 2014
UEFA Europa League Round of 16 draw…
Slovan Liberec/AZ v Anzhi Makhachkala/Genk
Lazio/Ludogorets v Dynamo Kiev/Valencia
FC Porto/Eintracht Frankfurt v Swansea/Napoli
Chornomorets/Lyon v Viktoira Plzen/Shakhtar Donetsk
Maribor/Sevilla v Real Betis/Rubin Kazan
Dnipro/Spurs v PAOK/Benfica
Maccabi Tel-Aviv/Basel v Ajax/RB Salzburg
Juventus/Trabzonspor v Esbjerg/Fiorentina
First legs to be played 13th March, 2014; Second legs to be played 20th March, 2014