Portsmouth will face seven-time European champions AC Milan in the group stages of the UEFA Cup.
Harry Redknapp's side booked their place in the group stages after overcoming Portuguese outfit Vitoria Guimaraes in extra-time during last week's first round and have been rewarded with a tie against the pre-tournament favourites in a difficult looking Group E.
Pompey will also take on Dutch side Heerenveen, Bundesliga outfit Wolfsburg and SC Braga of Portugal as they attempt to finish in the top three of a five-team group in order to progress to the last 32 stage.
Elsewhere, Manchester City have also been handed a series of tricky ties after being drawn in the same group as Schalke, Paris St Germain, Racing Santander and FC Twente.
Both Schalke and Twente - who are coached by former England manager Steve McClaren - dropped into the UEFA Cup reckoning after losing to Arsenal in the third qualifying round of the Champions League.
Under-pressure Tottenham manager Juande Ramos has reason to be cheerful after his struggling side were handed a less daunting set of Group D fixtures against Spartak Moscow, Udinese, Dinamo Zagreb and NEC Nijmegen.
Ramos has twice won the competition with former club Sevilla, but has seen his future come into question following Spurs' worst start to a domestic season in almost 100 years.
Aston Villa appear to have been handed a sterner test with in-form German side Hamburg, European heavyweights Ajax and Slavia Prague all lying in wait alongside MSK Zilina of Slovakia.
The first round of games will take place on October 23.
UEFA Cup group stage draw:
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, SC Braga, Portsmouth, Wolfsburg.
Group F: Hamburg, Ajax, Slavia Prague, Aston Villa, MSK Zilina.
Group G: Valencia, Club Brugge, Rosenborg, FC Copenhagen, Saint-Etienne.
Group H: CSKA Moscow, Deportivo La Coruna, Feyenoord, Nancy, Lech Poznan.