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.
Adams said: "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 continued: "He is obviously not happy about it and so we'll get it sorted out and make sure we do the best by him."
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."
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