Pompey are lining-up a pre-season friendly with Bournemouth – but only if Lee Bradbury’s League One promotion-chasers fail to reach the Championship.
The south-coast clubs have been summer opponents with increasing regularity over the years.
A Marc Wilson penalty separated the teams last season in a 1-0 win for the Blues.
Now the pair are poised to meet again.
Talks have already been held between Steve Cotterill and opposite number Bradbury.
But a date has still to be finalised as Pompey put the finishing touches to their pre-season tour to America.
Meanwhile, Bournemouth are currently in a play-off spot, putting them in contention for a Championship place next term.
Should that happen, they will find themselves in the same league as the Blues.
And that would see the fixture scrapped altogether.
Cotterill said: ‘I would want probably five to six games in pre-season.
‘We will probably play Bournemouth in one of those.
‘I have pencilled one in with them and been speaking to Lee Bradbury.
‘He actually thinks he is being a bit of a pain because he keeps contacting me.
‘I’ve actually said to him I’m a bit of a pain because I can’t actually say when we can play them at this moment in time.
‘We won’t play if they get promoted – that’s for certain – because they’ll be in the same league as us. But we’ll pencil that one in at the minute.’
When the south-coast clubs met in 2008, Harry Redknapp’s side ran out 4-1 winners.
It proved to be Sulley Muntari’s last-ever Pompey appearance, while Ritchie de Laet turned out for the hosts on trial.
The season before that, Lomana Lualua scored a hat-trick in a 4-1 triumph.
That proved to be his farewell appearance, moving to Olympiakos the following day.
They didn’t face each other in the 2009 pre-season when Paul Hart was boss.
But Cotterill took his side there last year, just days after returning from America and Canada.
They won 1-0 thanks to Wilson in what was their penultimate friendly of the summer.
Meanwhile, Cotterill revealed nothing yet has been finalised over any non-league opposition this summer.
The Hawks have become a regular fixture, albeit part of the agreement which saw them provide their ground to the club for reserve matches.
In recent years the Blues have visited Gosport Borough, Basingstoke and Eastleigh, too.
At present, though, nothing has been organised.
Although Pompey’s boss hasn’t ruled out the prospect.
He added: ‘We haven’t done anything with that one at the moment because it will be time restricting.
‘We need to make sure we get America right first.’