Standard Liege face a quickfire return to Merseyside after drawing Everton in the Uefa Cup first round.
Tricky first round tests for Toffees and Pompey
Standard Liege face a quickfire return to Merseyside after drawing Everton in the Uefa Cup first round.
The Belgian champions dropped into the competition after suffering a narrow 1-0 aggregate defeat to the Toffees' city rivals Liverpool in the final qualifying round of the UEFA Champions League.
FA Cup winners Portsmouth have been handed a tricky tie against Portuguese outfit Vitoria SC.
The Guimaraes-based club finished third in their domestic division last season and will provide stiff opposition to Harry Redknapp's men.
Aston Villa's reward for making it through the qualifying rounds is a trip to Bulgaria to tackle Litex Lovech.
Martin O'Neill's men overcame FH Hafnarfjordur to reach this stage of the tournament.
They were joined in the first round draw by fellow qualifiers, and Premier League rivals, Manchester City.
The Blues made hard work of seeing off Danish side FC Midtjylland on Thursday but their penalty shoot-out success sees them pitched against Cypriot side Omonia.
Carling Cup glory saw Tottenham book their place in European competition and Juande Ramos will come face-to-face with Polish champions Wisla Krakow.
SPL side Motherwell face a daunting tie against French club Nancy, with Pablo Correa's men having claimed a fourth place finish in Ligue 1 last season.
Eircom League side St Patrick's Athletic will face German club Hertha Berlin following a 4-3 aggregate win over Swedish side Elfsborg.
Other games of note see Serie A giants AC Milan face FC Zurich of Switzerland, while Udinese take on Borussia Dortmund.
Ajax face Serbian side Borac Cacak and Steve McClaren's FC Twente have drawn French opposition in the form of Rennes.
Full draw for the first round of the 2008/09 Uefa Cup is as follows:
AC Milan v FC Zurich
Politehnica Timisoara v Partizan Belgrade
Hertha Berlin v St Patrick's
Banik Ostrava v Spartak Moscow
Metalist Kharkiv v Besiktas
Portsmouth v Guimaraes
Kayserispor v PSG
Sevilla v SV Red Bull Salzburg
Wolfsburg v Rapid Bucharest
Sampdoria v FBK Kaunas
Maritimo v Valencia
Dinamo Zagreb v Sparta Prague
Man City v Omonia Nicosia
Young Boys v Club Brugge
Nancy v Motherwell
Everton v Standard Liege
Napoli v Benfica
AC Bellinzona v Galatasaray
NEC v Dinamo Bucuresti
Racing Santander v FC Honka
APOEL Nicosia v Schalke
Litex Lovech v Aston Villa
FK Austria Magna v Lech Poznan
Vitoria Setubal v Heerenveen
SK Brann v Deportivo La Coruna
Slavia Prague v Vaslui
Slaven Koprivnica v CSKA Moscow
Brondby v Rosenborg
Cherno More v Stuttgart
Rennes v FC Twente
Ajax v Borac
Tottenham v Wisla Krakow
FC Copenhagen v FC Moscow
MSK Zilina v Levski Sofia
Borussia Dortmund v Udinese
Braga v Artmedia Petrzalka
Feyenoord v Kalmar FF
Hamburg v Unirea Urziceni
Hapoel Tel-Aviv v Saint Etienne
FC Nordsjaelland v Olympiakos
The first legs of these ties are to be played on 18th September, with the return legs on 2nd October.
