Portsmouth chief executive Peter Storrie admits drawing Italian giants AC Milan in Europe is a "dream come true" for the club.
The FA Cup holders will also play Heerenveen, Braga and Wolfsburg in Group E of the UEFA Cup but the visit of the seven-time European Cup winners on November 27 will create the most excitement.
"As a tie it is a dream come true for our fans - and for everybody else associated with the club, certainly the players," said Storrie.
"Hosting AC Milan at Fratton Park is just like an old-fashioned cup-tie - with, hopefully, a giant-killing on the end of it."
Manchester City will come up against former England manager Steve McClaren's FC Twente in Group A of the competition.
McClaren's side have already been beaten by Arsenal this season in a Champions League qualifier and will face another stiff test against Mark Hughes' men. Schalke, Paris St Germain and Racing Santander make up the group.
"I've just come back to England to catch up on football here, and the signings Man City have made are massive and they are expected to do very well. It should be a fantastic occasion for us," McClaren told Sky Sports News.
"We had a fantastic night last Thursday, beating Rennes (to reach the group phase). We've taken the club into an area they have never been before, and hopefully things can only get better."
Meanwhile, Aston Villa will face German league leaders Hamburg, Dutch giants Ajax, Slavia Prague and MSK Zilina in a difficult-looking Group F, while struggling Tottenham will face Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen in Group D.
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