In total 12 senior players from Danny Cowley’s side – including those currently on loan at Fratton Park – will see their existing deals expire at the end of the season – with key players such as Sean Raggett, Marcus Harness and Michael Jacobs among them.
Meanwhile, across the EFL, there are plenty of former Blues stars in a similar boat to the present Fratton Park crop.
With another busy summer of transfer activity expected, could Cowley bring one of these potential free agents back to PO4?
You can decide as we take a look at the 23 former Pompey men who are set to be out of contract at the end of the campaign.
17. Ryan Allsop - Derby
Allsop was brought in as an emergency loan for the Blues’ two play-off semi-finals against Plymouth in the 2015-16 season. Now at Derby, questions are in the air about his future, with the Rams’ long-term status unclear. Photo: Joe Pepler
18. Dan Potts - Luton
The left-back was on loan at Fratton Park between November and December 2013, only playing five times. The 27-year-old has struggled for game time this term, making only five appearances in the Championship to date. Photo: Nigel Keene
19. Gareth Evans - Bradford
The former Pompey favourite had struggled at Valley Parade under former boss Derek Adams but has since regained his place in the team under new manager Mark Hughes. Photo: Graham Hunt
20. Lewis Ward - Swindon
The former on-loan Exeter keeper failed to make an appearance for Pompey last term and would later join Swindon on a year-long deal. Yet, he has been second choice behind Jojo Wallacott and has made only five outings in League Two this season. Photo: Jason Brown