Swansea have been handed a tough draw against Napoli in the last 32 of the Europa League.
Rafa Benitez's side, eliminated from the Champions League despite finishing on 12 points in a group featuring Arsenal, will go to Wales for the first leg on February 20 before hosting the return a week later.
Tottenham, who parted company with Andre Villas-Boas minutes before the draw, will come up against another of their former managers in the second round after they were paired with Juande Ramos' Ukrainians Dnipro.
The draw for the last 16 was also made at UEFA headquarters in Nyon, and both Premier League representatives could meet Portuguese opponents if they reach that stage.
Spurs will face last year's runners-up Benfica or Greek side PAOK if they get past Dnipro, while Swansea's reward for beating Napoli would be a tie with Porto or Eintracht Frankfurt.
Dnipro v Tottenham
Real Betis v Rubin Kazan
Swansea v Napoli
Juventus v Trabzonspor
Maribor v Sevilla
Plzen v Shakhtar Donetsk
Chornomorets Odessa v Lyon
Lazio v Ludogorets
Esbjerg v Fiorentina
Ajax v Salzburg
Maccabi Tel Aviv v Basel
Porto v Eintracht Frankfurt
Anzhi v Genk
Dynamo Kiev v Valencia
PAOK v Benfica
Slovan Liberec v AZ
Liberec/AZ v Anzhi/Genk
Lazio/Ludogorets v Dynamo Kiev/Valencia
Porto/Frankfurt v Swansea/Napoli
Odesa/Lyon v Plzen/Shakhtar
Maribor/Sevilla v Real Betis/Rubin Kazan
Dnipro/Tottenham v PAOK/Benfica
Maccabi/Basel v Ajax/Salzburg
Juventus/Trabzonspor v Esbjerg/Fiorentina