Of the four English sides in the draw, Pompey were handed the most eye-catching match-up by coming up against 2007 Champions League winners AC Milan.

The south coast side were placed alongside the Italian giants in Group E with Heerenveen, Braga and Wolfsburg.

Pompey will play each side once - with two home and two away fixtures, with the first against Braga in northern Portugal on Thursday October 23.

After a break on Matchday Two, Milan visit Fratton Park on Thursday November 27 and Pompey then travel to face Wolfsburg in Germany seven days later.

Harry Redknapp's men conclude their group challenge at home to Heerenveen on Wednesday December 17.

Pompey chief executive Peter Storrie was delighted with his side's draw.

"As a tie it is a dream come true for our fans - and for everybody else associated with the club, certainly the players," he said.

"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."

Struggling Tottenham will face Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen.

Juande Ramos, who guided Sevilla to UEFA Cup wins in 2006 and 2007, at least saw Spurs receive the fillip of a top seeding in Tuesday's draw, meaning they avoided some of the top-ranked sides such as his former club and AC Milan.

Tottenham were placed in Group D and will start their challenge away to Italian Serie A outfit Udinese on Thursday October 23.

Next up is a home tie against Croatia midfielder Luka Modric's former club Dinamo Zagreb on Thursday November 6.

Three weeks later, Spurs travel to Holland to face NEC Nijmegen and after a break from European action on Matchday Four, the group concludes at home to Spartak Moscow on either December 17 or 18 (date yet to be confirmed).

Striker Roman Pavlyuchenko, who left Spartak for White Hart Lane in the summer transfer window, will not be able to play against his former team-mates as he is cup-tied.

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 Saint-Germain and Racing Santander make up the group.

City will not be involved on Matchday One on October 23. They will return to European action against Twente at Eastlands on November 6, before travelling to play Schalke three weeks later.

PSG are the visitors to the City of Manchester Stadium on Wednesday December 3, and the group concludes with City away to Racing Santander on Thursday December 18.

Twente boss McClaren is already looking forward to the meetings with City and Schalke - now coached by his predecessor Fred Rutten.

"It's a fantastic draw for the fans, for the club and for the players," he told Sky Sports News.

"It's one of the toughest draws, but we've got a great draw and it's very exciting."

Asked for his reaction to coming up against City, McClaren added: "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.

"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 host four-time European champions Ajax and will also travel to face Hamburg - now managed by former Tottenham coach Martin Jol - in Group F.

Czech outfit Slavia Prague and MSK Zilina of Slovakia complete the pool.

The clash with Hamburg will see Jol reacquainted with English opposition a year after he was controversially sacked by Spurs.

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 good a squad not to do so but it is good to see Martin doing very well."

Jol feels Villa will pose the biggest threat to his side in Group F and told Hamburg's official website: "Ajax are a great team, but Aston Villa are for me the top favourites in the group.

"Slavia Prague are current champions and have strengthened and MSK Zilina are a very compact team who sit second in the Slovakian league table. We are looking forward to these matches."

Sporting director Dietmar Beiersdorfer admitted it was a tough draw, but backed Hamburg to reach the knock-out stages.

He said: "It is definite that we will have to call on all our reserves in order to make it to the next round. But we have recently acquired a lot of self-belief. So we will achieve this goal."

UEFA Cup draw in full:

Group A: Schalke, Paris St Germain, MANCHESTER CITY, Racing Santander, FC Twente.

Group B: Benfica, Olympiacos, Galatasaray, Hertha Berlin, Metalist Kharkiv.

Group C: Sevilla, Stuttgart, Sampdoria, Partizan Belgrade, Standard Liege.

Group D: TOTTENHAM, Spartak Moscow, Udinese, Dinamo Zagreb, NEC Nijmegen.

Group E: AC Milan, Heerenveen, Braga, PORTSMOUTH, Wolfsburg.

Group F: Hamburg, Ajax, Slavia Prague, ASTON VILLA, MSK Zilina.

Group G: Valencia, Club Bruges, Rosenborg, FC Copenhagen, St Etienne.

Group H: CSKA Moscow, Deportivo La Coruna, Feyenoord, Nancy, Lech Poznan.

Each team plays two matches at home and two away, with the top three teams from each group qualifying for the last 32.

Man City's UEFA Cup Group A fixtures: Nov 6, FC Twente (home); Nov 27, Schalke (away); Dec 3, PSG (home); Dec 18, Racing Santander (away).

Spurs' UEFA Cup Gp D fixtures: Oct 23, Udinese (away); Nov 6, D Zagreb (home); Nov 27, NEC Nijmegen (away); Dec 17/18, Sp Moscow (home).

Pompey's UEFA Cup Group E fixtures: Oct 23, Braga (away); Nov 27, AC Milan (home); Dec 4, Wolfsburg (away); Dec 17, Heerenveen (home).

Villa's UEFA Cup Group F fixtures: Oct 23, Ajax (home); Nov 6, Slavia Prague (away); Dec 4, MSK Zilina (home); Dec 17, Hamburg (away).