AC Milan have drawn Swiss side FC Zurich in the first round of the UEFA Cup, while Napoli face a fascinating test against Benfica, Udinese play Borussia Dortmund and Sampdoria have been paired with Kaunas.
Milan are amongst the favourites to lift the UEFA Cup, the one major international club trophy which has eluded them, after Fiorentina pipped them to the final UEFA Champions League spot in Serie A last term.
And Ancelotti's men will begin their campaign against Zurich, who knocked Empoli out of the competition at this stage last term.
Having battled through the Intertoto Cup and demolished Albanians Vllaznia Shkoder 8-0 in the preliminary round, Napoli weren't in the seeding bracket and feared a tough test.
And they got just that as the 1989 winners will face Portuguese giants Benfica in one of the ties of the round.
Sampdoria fell to Danish side Aalborg at this stage last season but will feel that they can go much further when they face FBK Kaunas.
But Walter Mazzarri's men would have taken note of the Lithuanian outfit after they stunned Glasgow Rangers in the Champions League preliminaries before getting knocked out.
The final Italian side to learn their fate were Pasquale Marino's Udinese and they will count themselves highly unfortunate to face German giants and former European champions Borussia Dortmund.
Ties will be played on 18 September and 2 October.
UEFA Cup First Round draw
First leg: 18 September
Second leg: 2 October
AC Milan v FC Zurich
FC Timisoara v Partizan Belgrade
Hertha Berlin v St Patrick's Athletic
Banik Ostrava v Spartak Moscow
Metalist Kharkiv v Besiktas
Portsmouth v Vitoria Guimaraes
Kayserispor v PSG
Sevilla v Salzburg
Wolfsburg v Rapid Bucharest
Sampdoria v Kaunas
Maritimo v Valencia
Dinamo Zagreb v Sparta Prague
Manchester City v Omonia Nicosia
Young Boys Berne v Club Brugge
Nancy v Motherwell
Everton v Standard Liege
Napoli v Benfica
Bellinzona v Galatasaray
NEC Nijmegen v Dinamo Bucharest
APOEL v Schalke
Litex Lovech v Aston Villa
Austria Vienna v Lech Poznan
Vitoria Setubal v Heerenveen
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 FK Borac
Tottenham Hotspur v Wisla Krakow
FC Copenhagen v FC Moscow
Zilina v Levski Sofia
Borussia Dortmund v Udinese
Braga v Artmedia Bratislava
Feyenoord v Kalmar
Hamburg v Unirea Urziceni
Hapoel Tel-Aviv v Saint-Etienne
FC Nordsjaelland v Olympiakos
Source: C4 Football Italia
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