Uefa Cup draw
Portsmouth have been drawn in the same Uefa Cup group as AC Milan, while Aston Villa, Tottenham and Manchester City have also been given tough opposition.
Aston Villa will play Ajax and Hamburg and Spurs' main threat is likely to come from Spartak Moscow and Udinese.
Pompey must also overcome Heerenveen, SC Braga and Vfl Wolfsburg.
But City, who play Schalke O4, Paris St Germain, Racing Santander and former England boss Steve McClaren's FC Twente side, will face the stiffest test.
Each team is in a five-team group and will play two opponents at home and the other two away, with the opening games to be played on 23 October.
Three teams from each group qualify for the next knockout round.
The final is in Istanbul on 20 May.
McClaren, whose side lost to Arsenal in the qualifying rounds for the Champions League, is looking forward to facing more English opposition.
"I've just come back to England to catch up on football here, and the signings City have made are massive and they are expected to do very well," the former Middlesbrough boss said. "It should be a fantastic occasion for us.
"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."
More follows.
Group A
Schalke 04
Paris St Germain
MANCHESTER CITY
Racing Santander
FC Twente
Group B
Benfica
Olympiakos
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
Vfl 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
Deportiva La Coruna
Feyenoord
Nancy
Lech Poznan
