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.
1. Michael Smith - Rotherham
The striker is Rotherham’s top scorer, netting 17 times in 38 League One outings this season. Yet he finds himself out of contract in the summer and has recently admitted he is prioritising promotion rather than focusing on contract talks. Photo: George Wood
2. Marc McNulty - Reading
The Scot is on loan at Dundee United, the fifth club he has spent time with since he joined Reading in 2018. The striker has revealed he would rather be on the dole than return to the Madejski Stadium at the end of the season. Photo: Joe Pepler
3. Jed Wallace - Millwall
Wallace has attracted interest as far as Turkey for his services after an outstanding season in the Championship. He has 15 goals and assists in 32 league games in the second tier so far this term. Photo: Joe Pepler
4. David Wheeler - Wycombe
The 31-year-old has played a key role in Wycombe’s rise in recent years but has been in and out of Gareth Ainsworth’s side this season, scoring just twice in 24 outings. Photo: Will Matthews