"We are looking for a memorable European night under the Fratton Park floodlights but we've already had two silly kick-off times.
"It was still light when we started against Vitoria at Fratton Park and supporters struggled to get there from work.
"Then in Portugal the players did not get back to the hotel until 2.30am after the game, just a couple of days before we had to play Stoke in the Premier League.
"The league is always my priority. We are going well again after a tough start this year but you've always got to watch your position because it's a very tight competition, tighter than ever.
"But AC Milan in a European competition is a one-off occasion. That should be a fabulous night.
"Who could imagine the thought of Paulo Maldini, Ronaldinho, Kaka and all those running out to play here but who could have imagined Portsmouth winning the FA Cup and having four players in the England squad?
"Now it could all happen."
Pompey play the seven-times European Cup winners - who were knocked out of the Champions League in the second round by Arsenal last term and finished only fifth in Serie A - on Thursday, November 27.
First, though, Pompey face a quick return trip to Portugal to begin their second round group campaign on October 23 at Sporting Braga.
The top three in the five-team group go through to the next knockout stage where third-place finishers in the Champions League groups will join them to make up a UEFA Cup last 32.
Pompey chief executive Peter Storrie, who was in Nyon for the draw, said: "It is a well-balanced group we are in and there are 40 quality teams still left in the competition but the AC Milan match is outstanding, a mouth-watering prospect.
"It must be a dream come true for our fans - and for everybody else associated with the club, certainly the players.
"It's fantastic and although I know some supporters will be a little disappointed 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."