Tottenham will come face to face with former manager Juande Ramos after they were drawn against Ukrainian outfit FC Dinipro in the last 32 of the Europa League.
Spurs, who announced their decision to terminate the contract of manager Andre Villas-Boas this morning, will go up against the man who took charge at White Hart Lane between 2007 and 2008.
Tottenham were one of only two clubs to have made it through the Europa League group stages with a 100% win record, however they will now continue on in the competition without the Portuguese boss.
Ramos, who was sacked by chairman Daniel Levy after overseeing Tottenham's worst ever start to a league campaign with eight straight defeats in 2008, has been in charge of Dnipro since 2010 and his side currently sit in 4th place in the Ukrainian top tier.
If Tottenham make it through the two ties agains Dnipro they will be rewarded with a last 16 tie against Portuguese giants Benfica, who drew PAOK of Greece.
The only other remaining British club in the draw, Swansea, will go up against Napoli, who dropped down into the Europa League following their elimination from the Champions League, having missed out on a place in the last 16 of that competition by virtue of goal difference to Arsenal and Borussia Dortmund.
Juventus, another club to drop down from the Champions League, will go up against Turkish outfit Trabzonspor, while Ajax face Salzburg and Porto face Eintracht Frankfurt.
Other noticeable ties include Real Betis v Rubin Kazan and Maccabi Tel-Aviv v Basel.
The last 32 games will take place on February 20 and 27, while the last 16 fixtures will take place on March 13 and 20.
Europa League last 32 draw
Dnipro v Tottenham
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 FC Salzburg
Maccabi Tel-Aviv v Basel
Porto v Eintracht Frankfurt
Anzhi v Genk
Dynamo Kiev v Valencia
PAOK v Benfica
Slovan Liberec v AZ Alkmaar
Europa League last 16 draw
Slovan Liberec /AZ Alkmaar v Anzhi/Genk
Lazio/Ludogorets v Dynamo Kiev/Valencia
Porto/Eintracht Frankfurt v Swansea/Napoli
Chornomorets/Lyon v Viktoria Plzen/Shakhtar Donetsk
Maribor/Sevilla v Real Betis/Rubin Kazan
Dnipro/Tottenham v PAOK/Benfica
Maccabi Tel-Aviv/Basle v Ajax/FC Salzburg
Juventus/Trabzonspor v Esbjerg/Fiorentina