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.
9. Stephen Henderson - Charlton
The keeper, signed by the Addicks in the summer, has found himself as second choice to former Pompey stopper Craig MacGillivray at Charlton throughout the season and has managed only two outings to date. Photo: Colin Farmery/Portsmouth FC
10. Marlon Pack - Cardiff
The Pompey-born midfielder has established himself as a solid Championship player but has struggled for game time this term, with his last outing coming in a 3-2 defeat to Bristol City in January. Pack, now 31, left Pompey permanently in May 2011 after two appearances. Photo: Stu Forster
11. Ben Thompson - Gillingham
The former Pompey favourite made the shock move to Gillingham on the final day of the January transfer window, linking up with former boss Neil Harris at Priestfield. The midfielder penned a deal until the end of the season and has been involved heavily for the Gills, appearing 11 times since his arrival. Photo: Joe Pepler
12. Caolan Lavery - Bradford
Lavery scored four times in 13 outings during his three-month loan at Fratton Park between October 2015 and January 2016. The striker has netted just once this term for Bradford and looks to be closing in on an exit from Valley Parade in the summer. Photo: Joe Pepler