Portsmouth have been drawn against AC Milan in the most eye-catching fixture of the Uefa Cup draw.
Meanwhile Tottenham will face Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen in the next stage of their Uefa Cup campaign.
Spurs are bottom of the Premier League after a miserable start to the season but they reached the group phase of the Uefa Cup with victory against Wisla Krakow over two legs.
Juande Ramos' side at least received the fillip of a top seeding in today's draw, meaning they avoided some of the top-ranked sides such as AC Milan and Sevilla in their group.
They were placed in Group D and will play each other side once - with two home and two away fixtures - and the clash against Dinamo Zagreb will see summer signing Luka Modric come up against his old club.
Of the three other English sides in the draw, Portsmouth were handed one of the most eye-catching match-ups by coming up against 2007 Champions League winners AC Milan.
Pompey were placed alongside the Italian giants in Group E with Heerenveen, Braga and Wolfsburg.
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.
Aston Villa will face Martin Jol's Hamburg, Ajax, Slavia Prague and MSK Zilina in Group F.
Portsmouth chief executive Peter Storrie was delighted with his side's draw.
Storrie told Sky Sports News: "It is a good group all the way round.
"If you look at the teams there are 40 good sides in the Uefa Cup, it is a tough competition to come through.
"But we will enjoy it and I am sure our fans will pinch themselves thinking Portsmouth Football Club are going to play AC Milan in European competition."
Twente boss McClaren was 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."
The full draw for the UEFA Cup Group Stage is as follows:
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