Manager: Carlo Ancelotti
Ground: San Siro (Capacity 82,955)
Major Honours: 17 League Titles, 7 European Cups, 5 Italian Cups
Qualified for UEFA Cup by: Finishing 5th in Serie A
First Round Result: Beat FC Zurich 4-1 on aggregate
Key Players: Kaka, Ronaldinho, Genarro Gattuso
Associazione Calcio Milan are one of the biggest clubs in the world and a team that Pompey fans could only dream about watching at Fratton Park just a couple of years ago.
Their European success is only bettered by Real Madrid and domestic success only inferior to Juventus. Their squad is littered with some of the biggest stars in world football such as twice world player of the year Ronaldinho, last year's world player of the year Kaka and one of the best defenders of all time in Paolo Maldini.
Looking further down their squad list you'll see players such as rising star Alexandre Pato, set-piece expert Andrea Pirlo, former Arsenal midfielder Mathieu Flamini and of course, Andriy Shevchenko.
It was only just over a year ago that they defeated Liverpool to win their 7th European Cup but the calciopoli scandal has tarnished the reputation of this great club and may be one of the reasons for two below-par league seasons which has meant the Rossoneri taking part in the UEFA Cup this year as they could only manage 5th place in Serie A.
Even though Milan and Pompey are miles apart in terms of history and quality the two clubs do share a couple of links. Mark Hateley was sold to AC Milan in 1984 and stayed there for three years whilst Richard Hughes is an avid fan of the Italian club and will relish the prospect of playing against his boyhood heroes.
AC Milan are one of the favourites to win the UEFA Cup and will probably top Group E. However, the stars of such a glamorous club won't relish a trip to Fratton Park so, who knows? Maybe Pompey can claim the biggest scalp in their history come the 27th of November.
Manager: Trond Sollied
Ground: Abe Lenstra Stadion (Capacity 26,100)
Nickname: Pride of Friesland
Major Honours: None
Qualified for UEFA Cup by: Finishing 5th in Eredivisie
First Round Result: Beat Vitoria Setubal 6-2 on aggregate
Key Players: Danijel Pranjic, Mika Vayrynen, Bonaventre Kalou
You have to commend Heerenveen for what they have achieved in recent years. Whilst Heerenveen is only a small town with a population of around 43,000 people, the club has enjoyed relative success in their league as they look to break the hold that the "big three" of PSV Eindhoven, Ajax and Feyenoord have on the Eredivisie.
Heerenveen are most famous for producing some top quality players. Ruud van Nistelrooy, Klaas-Jan Huntelaar, Jon Dahl Tomasson and Afonso Alves have all been on the books of the Friesland club.
Most Pompey fans will see the home clash with the Dutch side on December 17th as the easiest game in the group but there can be no doubts that Heerenveen will also fancy their chances seeing as they have a reputation of succeeding against the odds.
Manager: Jorge Jesus
Ground: Estadio Municipal de Braga (Capacity 30,154)
Nickname: The Arsenalists
Major Honours: Portuguese Cup Winners 1966
Qualified for UEFA Cup by: Beating Sivasspor 5-0 on aggregate in Intertoto Cup, then defeated Zrinjski Mostar 3-0 on aggregate in 2nd qualifying round
First Round Result: Beat Artmedia Petrzalka 6-0 on aggregate
Key Players: Luis Aguiar, Wason Renteria, Roland Linz
I had a feeling that we would draw Braga in the group stages having just knocked their fierce rivals out of the competition. This club have been the closest to breaking the dominance of the Portuguese "big three" over the years, with three consecutive fourth place finishes from 2005-2007.
There is strong debate in Minho as to who the fourth biggest club in Portugal are. Guimaraes fans claim that they are better supported than any other club outside the "big three" but Braguistas believe that they have more fans and are more passionate to boot.
Braga play at the Estadio Municipal de Braga (now known as Estadio AXA) which is famous for being built in a quarry and only having two large stands either side of the pitch, so there are no seats behind the goals.
Having had an early scour of their forums it seems that Braguistas believe that they will beat us on their own turf. I watched them play Guimaraes on Monday and Braga were certainly the superior team in that game despite a bad start to their league campaign.
SC Braga are nicknamed "The Arsenalists" after their coach travelled to Highbury and then changed their home strip to the famous red and white of Arsenal. Come the 23rd of October we shall see if they are anywhere near as good as the Gunners.
Manager: Felix Magath
Ground: Volkswagen-Arena (Capacity 30,000)
Nickname: The Wolves
Major Honours: None
Qualified for UEFA Cup by: Finishing 5th in German Bundesliga
First Round Result: Beat Rapid Bucharest 2-1 on aggregate
Key Players: Josue, Jacek Krzynowek, Grafite
Wolfsburg is the home of Volkswagen and was built by the Nazis during World War II as a vehicle manufacturing city. Because Wolfsburg is such a young city it is no surprise to see that the football club doesn't really have any notable history.
However, Wolfsburg have had their fair share of big names to wear the white and green halved shirt such as Stefan Effenberg, Claudio Reyna, Kevin Hofland and Martin Petrov.
The biggest name to be affiliated with the German club that will be most recognised by Pompey fans is Andres D'Alessandro. The little Argentinian magician arrived from Wolfsburg in 2006 to play a huge part in our escape from relegation and has now moved on to Brazillian club Internacional.
In my opinion, Wolfsburg were the toughest side we could have drawn from pot five. Felix Magath is a very good manager having taken Bayern Munich to two Bundesliga titles whilst Polish winger Krzynowek is a major threat. Pompey will do very well to defeat the Wolves on their home turf but I'm sure the fans will enjoy the trip to Germany on December the 4th, whatever the result.