Harry Redknapp's reward for the 4-2 triumph over Vitoria Guimaraes is a fixture with the European giants in Group B.
They will also come up against more Portuguese opposition in the form of SC Braga, neighbours of the defeated Guimaraes.
Dutch side Heerenveen and German outfit VfL Wolfsburg complete a tantalising draw for Pompey.
But it will be Milan which will have drawn the biggest cheer among Blues fans with the delicious prospect of Kaka and Co in opposition.
Football chiefs will now meet to thrash out the order of the fixtures and who will have home advantage, the final details likely to be known soon.
>>> AC Milan will define glorious Pompey era - read Burton's Banter by clicking here.>>> Replay the UEFA Cup draw as it happened. Click here for more.UEFA CUP DRAW GROUP A: Schalke 04, Paris SG, MANCHESTER CITY, Racing Santander, FC Twente
GROUP B: Benfica, Olympiacos, Galatasaray, Hertha Berlin, Metalist Kharkiv
GROUP C: Sevilla, VfB Stuttgart, Sampdoria, Partizan Belgrade, Standard Liege
GROUP D: TOTTENHAM, Spartak Moscow, Udinese, Dinamo Zagreb, NEC Nijmegen
GROUP E: AC Milan, Heerenveen, SC Braga, PORTSMOUTH, VfL Wolfsburg
GROUP F: Hamburg, Ajax, Slavia Prague, ASTON VILLA, MSK Zilina
GROUP G: Valencia, Club Brugge, Rosenborg, FC Copenhagen, Saint-Etienne
GROUP H: CSKA Moscow, Deportivo La Coruna, Feyenoord, Nancy, Lech Poznan
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