Guy Whittingham and Stuart Gray have been told their jobs are under threat.
Administrator Trevor Birch has informed the duo that one of them will be made redundant at the end of the month.
Both serve as Michael Appleton’s first-team coaches.
However, in a bid to wrestle the club’s wage bill under control, one will have to leave Fratton Park.
Other backroom jobs at the Blues are also to go.
However, there will be no redundancies until after the season has been completed on Saturday.
In addition, Pompey’s players have been asked to take further pay reductions as Birch seeks to drive down the £12m annual wage bill.
The administrator will meet PFA representative Nick Cusack today for further discussions, following initial talks with the playing staff on Tuesday.
The news of the exit of either Whittingham or Gray follows another bleak day at Fratton Park.
Blues legend Linvoy Primus and club photographer Joe Pepler were on the latest list of casualties yesterday.
Now the attention will turn to the playing and backroom staff, with more departures expected at the end of this month.
Birch said: ‘It has been horrible dealing with this, as it always is in these situations.
‘However we are trying to get the costs down to a League One level and these actions have to be taken.
‘Guy and Stuart are under threat – unfortunately we can only afford one.
‘This is nothing about their ability as coaches, it is purely down to finances and costs need to be made on this side.
‘The decision will be made and one of them will leave at the end of the month.
‘Other backroom jobs are also under threat and discussions will continue.
‘It is horrendous making people redundant, I know, but it is about finances and I am afraid wages are a massive problem at this club.
‘We expect there to be around 10 redundancies in all, in this latest round.’
Of those scheduled for redundancy, just four have come among office staff.
Birch knows only too well his chief focus has to be slashing the player wage bill which totals £12m.
The deals of Jamie Ashdown, Ricardo Rocha and Benjani expire this summer but 14 senior first-team players are contracted for at least another 12 months.
Stephen Henderson will join West Ham when the transfer window reopens on June 9, while Jason Pearce is being pursued by Leeds.
That still leaves Birch with a wage bill he wants to slash to bring it down to £5m in League One.
At a meeting on Tuesday, players were asked to take pay cuts in addition to the deferrals they agreed to two months ago.
And Birch revealed discussions are continuing.
He added: ‘Negotiations are still going on with the players at this moment in time.
‘They have been requested to take further wage reductions, something which is very necessary.
‘I shall be meeting with the PFA representative Nick Cusack today.’