Jermain Defoe's revelation that he requires surgery on a calf injury has given manager Tony Adams a major selection dilemma ahead of Thursday night's UEFA Cup tie with AC Milan.
The operation would rule out Defoe for at least four weeks and leaves Adams, who is almost certain to be without star midfielder Lassana Diarra once again, desperately short of fire power.
The timing is catastrophic given defeat would leave the FA Cup winners struggling to qualify for the knockout stages after a 3-0 hammering by Portuguese side Braga in their opening Group E game last month.
Defoe had to come off at half-time in England's victory in Germany last Wednesday when he aggravated a problem which Pompey now admit he has had for some time. The £7.5million striker also missed Saturday's 2-2 home draw with Hull.
He is visiting a specialist to assess the full damage and fears an operation might be the only real remedy.
''I have had the problem for the past three games and it has got to the point that when I play I can't feel my foot because of the numbness,'' he said.
''I have had treatment including acupuncture but it is showing no signs of clearing up, and I know another England player who has had a similar problem and needed surgery to sort it out.
''It is only a minor operation but it could mean me missing out for at least four weeks.''
Adams confirmed Defoe would not be fit to face the Italian giants at Fratton Park.
''We'll know more about Jermain's situation soon. He's seeing a guy about it and no, he won't play against Milan,'' he said. ''He is obviously not happy about it and so we'll get it sorted out and make sure we do the best by him.''
Frenchman Diarra, meanwhile, is also consulting various specialists in England and his homeland about the ankle injury that has sidelined him since a tackle by West Ham's Scott Parker on November 15.
Adams said: ''He is seeing different people on Monday, Tuesday and Wednesday about it so he's got to be a doubt, but I'm not a doctor and can't comment on things I really don't know about.
''But I won't risk players who are not 100% fit. I did that myself as a player and you can't do yourself justice.''
Adams is more hopeful that skipper Sol Campbell (toe) and midfielder Niko Kranjcar (ankle) could return against Milan.
And Diarra's likely absence could give a dream chance to Richard Hughes who grew up in Milan supporting the Rossoneri.
But with fit-again David Nugent and on-loan Ben Sahar both ineligible after being left out of Pompey's initial UEFA Cup squad by former manager Harry Redknapp, it will leave Pompey worryingly short of striking options.
Adams has already stated he will give chances on Thursday to players like defender Hermann Hreidarsson and Kanu, who made major contributions to last season's FA Cup triumph but have since played only bit-part roles.
''We will be going in there to throw everything at AC Milan and give the Portsmouth supporters a great night,'' the Pompey boss said.
''The match is probably the most prestigious we'll ever play, a reward and a reflection on what we did last season, but for me Premier League wins are the priority.''