Managerless Tottenham Hotspur will face Ukrainian side Dnipro in the last 32 of the Europa League, while Swansea play host to European giants Napoli.
Dnipro, managed by former Spurs boss Juande Ramos, finished second in Group E and are fourth in the Ukrainian league. Former Blackburn striker Nikola Kalinic is on their books.
Swansea were handed a dream draw as they play Italian giants Napoli, who were unlucky to have exited the Champions League after finishing third in Group F despite winning four of their six group games. Rafa Benitez' side are second in Serie A and have a squad full of world class talent, including Pepe Reina, Gonzalo Higuain and Marek Hamsik.
Should Spurs and Swansea win their last 32 ties, they will play the winners of the PAOK Salonika v Benfica and Porto v Eintracht Frankfurt matches respectively.
Elsewhere, Juventus play Trabzonspor and the prospect of another trip to Turkey after losing to Galatasaray in their final Champions League group game which saw them fall into the Europa League.
Their is also the prospect of a Sevilla derby in the last 16, so long as Sevilla beat Slovenian side NK Maribor and Real Betis get past Rubin Kazan of Russia.
The first leg ties of the last 32 will take place on 20th February, with the second leg a week later. The last 16 matches will take place on 13th/20th March.
Last 32 draw
Dnipro v Tottenham Hotspur (return of Juande Ramos)
Real Betis v Rubin Kazan
Swansea City v Napoli
Juventus v Trabzonspor
NK Maribor v Sevilla
Viktoria Plzen v Shakhtar Donetsk
Chornomorets v Lyon
Lazio v Ludogorets
Esbjerg v Fiorentina
Ajax v Salzburg
Maccabi Tel-Aviv v Basel
Porto v Eintracht Frankfurt
Anji v Genk
Dynamo Kiev v Valencia
PAOK v Benfica
Slovan Liberec v AZ Alkmaar
Last 16 draw
Slovan Liberec/AZ Alkmaar v Anji/Genk
Lazio/Ludogorets v Dynamo Kiev/Valencia
Porto/Eintracht Frankfurt v Swansea City/Napoli
Chornomorets/Lyon v Viktoria Plzen/Shakhtar Donetsk
NK Maribor/Sevilla v Real Betis/Rubin Kazan
Dnipro/Tottenham Hotspur v PAOK/Benfica
Maccabi Tel-Aviv/Basel v Ajax/Salzburg
Juventus/Trabzonspor v Esbjerg/Fiorentina
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