Harry Redknapp is never slow to point out that when he took over as manager of Portsmouth for the first time their fixture list included matches against Walsall and Rotherham United rather than Chelsea and Liverpool. However, even he will be pinching himself after yesterday's draw for the group phase of the Uefa Cup sent AC Milan, the seven-times champions of Europe, to Fratton Park.

Until this season, the only Milans to have appeared at Portsmouth's antiquated home ground were Milan Mandaric, the former chairman, and Milan Baros, the Czech Republic striker who spent part of last season on loan at Fratton Park, but now the FA Cup holders can look forward to the visit of Kaká, Ronaldinho and Co to Hampshire on November 27 as well as matches against Braga, of Portugal, Wolfsburg, of Germany, and Heerenveen, of the Netherlands.

However, Redknapp called for a traditional kick-off time after television demands required early and late starts in the two legs of the first-round tie against Vitória Guimarães. “We've got a fantastic game, a dream tie, to put on for our fans and we need to make the best of it, with a 7.45 or 8pm kick-off,” he said. “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 Vitória at Fratton Park [at 6pm] 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. But AC Milan in a European competition is a one-off occasion. That should be a fabulous night.”

Although the fixture will be a novelty for most of those involved, Peter Crouch faced Milan as a substitute for Liverpool in the 2007 Champions League final in Athens, while Andriy Shevchenko and Mathieu Flamini, of Milan, will know what to expect at Fratton Park, having played there for Chelsea and Arsenal respectively.

Aston Villa also have an enticing home fixture against former European Cup winners, with Ajax their first opponents at Villa Park on October 23 in a tough-looking group that includes Hamburg, the leaders of the Bundesliga, who are coached by Martin Jol, the former manager of Tottenham Hotspur, Slavia Prague, of the Czech Republic, and MSK Zilina, of Slovakia.

“Ajax is a real mouth-watering tie,” Martin O'Neill, the Villa manager, said. “It's just absolutely brilliant to be part of it all and being back in European competition is fantastic news for the football club. Villa Park could be really rocking against Ajax in that opening game.

“If you look at some of the teams involved - for example AC Milan, Seville, Ajax - these are sides with a real pedigree. There are 10 or 12 teams still in the competition that could be contesting the Champions League.”

Tottenham are finding all their games difficult at the moment, so can expect hard going against Udinese, the joint leaders of Serie A, Spartak Moscow, Dynamo Zagreb, of Croatia - from whom they signed Luka Modric this year - and NEC Nijmegen, of the Netherlands. Roman Pavlyuchenko, the Russia striker whom Tottenham signed from Spartak, is not eligible to play against his former club, having played for them in their Champions League third qualifying round defeat by Dynamo Kiev.

Manchester City will be up against Twente, the Dutch club managed by Steve McClaren, the former England head coach, as well as Schalke, Paris Saint-Germain and Racing Santander.