Portsmouth chief executive Peter Storrie admits drawing Italian giants AC Milan in Europe is a "dream come true" for the club.
Pompey were placed alongside the 2007 Champions League winners in the draw for the group stage of the UEFA Cup.
The FA Cup holders will also play Heerenveen, Braga and Wolfsburg in Group E but the visit of the seven-time European Cup winners on No
vember 27 will create the most excitement.
Storrie said: "As a tie it is a dream come true for our fans – and for everybody else associated with the club, certainly the players.
"It's a fantastic prospect and although I know some supporters will be a little disappointed that we are not going to play in the San Siro, my thought is that it could be a half-empty stadium on the night and take something away from the occasion.
"Hosting AC Milan at Fratton Park is just like an old-fashioned cup-tie – with, hopefully, a giant-killing on the end of it."
Pompey will begin their campaign with a quick return to Portugal to play Braga, neighbours of Guimaraes, the side they beat last week in a first round tie that went beyond midnight.
Dutch side Heerenveen will be their other home opponents in the last match of the group stage, following a trip to Wolfsburg.
Struggling Tottenham will face Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen in Group D.
Spurs are bottom of the Premier League after a miserable start to the season but they reached the group phase with victory against Wisla Krakow over two legs.
Their clash against Dinamo Zagreb will see summer signing Luka Modric face his old club but fellow new boy Roman Pavyluchenko is cup-tied and cannot face former team Spartak.
Manchester City will come up against former England manager Steve McClaren's FC Twente in Group A.
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.
"We weren't ready for Arsenal, that shows the gap. We are a young side, inexperienced, especially in Europe, but we will just enjoy it. It is about the future for these young players."
Aston Villa will face German league leaders Hamburg, Dutch giants Ajax, Slavia Prague and MSK Zilina in a difficult-looking Group F.
The clash with Hamburg will see coach Martin Jol reacquainted with English opposition a year after he was controversially sacked by Tottenham.
Jol paid the price for a poor start to the season and Villa boss Martin O'Neill admits he felt sorry for the Dutchman.
O'Neill told Sky Sports News: "I think that everybody would say on reflection it was pretty rough in the sense that they finished, twice, fifth and the looked as if they would be challenging.
"Anyone can get off to a poor start, as Tottenham have done this season. I have no doubt that they will recover from that, they are too squad a squad not to do so but it is good to see Martin doing very well."
The full article contains 610 words and appears in The Scotsman newspaper.
