Paul Cook is to initiate his summer rebuilding programme by selling Adam Webster to Ipswich Town.
And with a fee believed to be well in excess of £500,000, he will be given the opportunity to dip into the transfer market.
As part of the agreement with the Championship side, Matt Clarke is to remain at Fratton Park on a permanent basis.
The 19-year-old has enjoyed an impressive season-long loan, even partnering Webster in the centre of defence on occasions.
It is understood personal terms have still to be agreed on the Ipswich deal, but no hitch is anticipated.
The potential deal is viewed by Cook as excellent value for the Blues.
That’s despite signalling the departure of their longest-serving player.
In addition, any funds handed down as part of the sale can aid a recruitment drive to boost chances of promotion next season.
Already Pompey’s boss is pursuing a number of targets, some involving transfer fees, as he seeks to make early signings during the close season.
At the top of his list is a striker and a goalkeeper, while more attacking midfield options are also high on the agenda.
Speaking earlier this week, Cook told The News: ‘Clarke has had 12 months with us and been an absolute credit, he is everything you want in a lad, an absolute diamond of a boy.
‘If we ever got him back it would only be for the benefit of our club.
‘A 19-year-old left-footed centre half would only get better and stronger.
‘He has been outstanding for us this season.’
Webster has enjoyed his finest season yet with the Blues, finally establishing himself in his preferred position of centre back.
He was heading out the Fratton exit at the end of the previous season before caretaker boss Gary Waddock restored him to the side.
After impressing in the final four matches at centre half, the youngster from West Wittering was handed a two-year deal last summer.
He has blossomed under Cook, making 35 appearances this term and scoring twice.
However, he missed Pompey’s play-off campaign with damaged ligaments to his left ankle.
Webster broke into the first-team back in January 2012 against West Ham when Michael Appleton was manager.
He has gone on to feature 81 times and score five goals, while also spending time on loan at Aldershot.
Clarke has made 34 appearances during his Fratton Park loan spell, netting once.
He has lined-up alongside the 21-year-old Webster in the centre of defence on 10 occasions this season.
Pompey’s chief executive Mark Catlin added: ‘Until the ink is dry on any signature on any contract, as a club we do not comment on it.’