Ricardo Rocha will be asked to make a final decision on his possible return to Pompey this week.
Blues boss Guy Whittingham wants the popular Portuguese defender back at Fratton Park for the new campaign but admits he needs to know one way or the other as he builds his squad for the new season.
Centre-back Rocha would add experience and an abundance of quality to the defensive options and would complete the rare feat of playing in all four divisions for the Blues if he decides to rejoin.
And while Whittingham is keen not to put pressure on his friend, he knows time is ticking if he must move on to other defensive targets.
Speaking after Pompey’s 4-2 friendly win at Bognor, Whittingham said: ‘By this weekend, we will know one way or the other whether Ric will be coming back.
‘He is aware of the situation.
‘That’s not to put him under pressure and he doesn’t feel under pressure but obviously at some stage we need to make a decision.
‘To be fair to Ric, he has always said “if you need to go out and get players in, do it”.
‘And I’m not going to say what the delay is – that’s down to him.
‘But I think we will know at the weekend one way or the other.’
While Whittingham remains optimistic fans’ favourite Rocha could yet return, he has ruled out the possibility of Shaun Cooper earning a deal. Cooper, who started his career at Pompey and returned last season on loan from Crawley, was hopeful he could sign a contract after returning during pre-season.
But Whittingham – who takes his squad to Essex for a pre-season trip this week – has decided to look elsewhere.
He said: ‘I just didn’t think it was our best option at the moment.
‘I think Coops is a good guy and he can play in different areas but where we are at the moment and where we are trying to go, he just wasn’t the right one.
‘It’s possible we might revisit it in the future but I can’t see Shaun being without a club before the season starts.
‘It was a difficult decision because he did very well for us last season.
‘There are other things that we’re trying to do that might come off and might not but that’s the decision we’ve made with Shaun.’
Whittingham also reaffirmed none of the other triallists who played against the Hawks or an Aldershot XI last week will be offered a contract, although striker Ryan Bird is expected to continue his trial period after he returns from holiday.
Whittingham said: ‘That will be it as far as the triallists are concerned.
‘There won’t be any of those guys coming back.
‘There were lots of reasons – finances, better options elsewhere or not quite being what we were looking for.’