Tottenham Hotspur face Georgian league champions Dinamo Tbilisi for a place in the Europa League group stage while Swansea City continental adventure continues against Petrolul Ploiesti.
The Swans, who qualified for their first European campaign for 22 years by winning last season's League Cup, overcame Malmo 4-0 on aggregate and will be favorites to continue their campaign against Romanian opposition currently managed by international legend Cosmin Contra.
Spurs meanwhile face a Tbilisi side ranking outside of the top 200 in Uefa's coefficient rankings in a tie that will represent the true failure of qualifying for this season's Champions League.
The draw may evoke memories of Spurs' 1973/74 Uefa Cup campaign where they defeat Tbilisi 6-2 on aggregate in the third round, a season during which they went on to reach the final, losing to Feyenoord over two legs.
With the tie coming amid the start of both side's Premier League campaign, managers Andre Villas-Boas and Michael Laudrup are likely to field weakened sides in the ties against opposition unlikely to provide a significant obstacle.
FA Cup winners Wigan Athletic are among the sides who have earned automatic qualification for the group stage.
The ties will be played on 22 and 29 August.
Europa League Play Off draw in full:
Kuban Krasnodar v Feyenood
Apollon Limassol v Nice
Elfsborg v FC Nodsjaelland
FK Jablonec v Real Betis
Molde FK v Rubin Kazan
Zulte Waregem v Apoel
Aktobe v Dynamo Kiev
Slack Wroclaw v Sevilla
Rijeka v VfB Stuttgart
Vojvodina FC Sheriff
Rapid Wien v Dila Gori
Swansea City v Petrolul Ploieşti
FC Salzburg v VMFD Zalgiris
Chornomorets Odesa v Skenderbeu
Trabzonspor v FC Kukesi
Tromso IL v Besiktas
Atromitos v AZ
Qarabag v Eintracht Frankfurt
Maccadi Tel-Aviv v PAOK
Esbjerg v Saint-Etienne
Pandurii Lignitul Targu v Braga
FH v Genk
FC Minsk v Standard Liege
ST.Gallen v Sparket Moskva
Grasshopper v Fiorentina
Maccabi Haifa FC v FC Astra
Udinese Calcio v FC Slovan Liberec
FC Dinamo Tbilisi v Tottenham Hotspur
Estoril Praia v FC Pasching
JK Nõmme Kalju v FC Dnipro Dnipropetrovsk
FK Partizan v FC Thun