Everton will have the chance to add to Belgian club Standard Liege's Merseyside misery after being drawn with them in the first round of the Uefa Cup.
David Moyes' team will face the team who were knocked out of the Champions League qualifiers by Liverpool, with the tie to be contested over two legs.
Harry Redknapp will test the European credentials of his Portsmouth side against Portuguese side Vitoria SC, who are also known as Guimaraes.
Portsmouth qualified for the competition after winning last season's FA Cup.
Manchester City will face Cypriot side Omonia. Mark Hughes' side came back from a 1-0 first-leg deficit to beat FC Midtjylland in Denmark last night after extra-time and penalties to secure their place in the first-round draw.
Aston Villa are to play Bulgarian outfit Litex Lovech and Tottenham will be up against Polish club Wisla Krakow.
Clydesdale Bank Premier League outfit Motherwell will play French club Nancy.
St Patrick's Athletic will face German side Hertha Berlin in the first round.
The eircom League outfit made the first round with a 4-3 aggregate win over Swedish side Elfsborg.
Former England coach Steve McClaren will see his FC Twente side up against French club Rennes.
McClaren had seen the Dutch club go out of the Champions League qualifiers after defeat by Arsenal.
Soccer-Uefa Cup first round draw:
AC Milan v FC Zurich
Politehnica Timisoara v Partizan Belgrade
Hertha Berlin v St Patricks
Banik Ostrava v Spartak Moscow
Metalist Kharkiv v Besiktas
Portsmouth v Guimaraes
Kayserispor v PSG
Sevilla v SV Red Bull Salzburg
Wolfsburg v Rapid Bucuresti
Sampdoria v FBK Kaunas
Maritimo v Valencia
Dinamo Zagreb v Sparta Prague
Man City v Omonia Nicosia
Young Boys v Club Brugge
AS 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 04
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 VfB 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 Olympiacos
Ties to be played 18 September and 2 October.
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