In total, 11 members of the Blues’ current squad’s deals expire – including the likes of Tom Naylor, Jack Whatmough and Ben Close.
Head coach Danny Cowley’s already confirmed that Duncan Turnbull’s time on the south coast has come to an end, having joined American outfit Las Vegas Lights on loan.
However, there are plenty of former Pompeymen in a similar situation.
A host of ex-Blues players’ contracts up and down the country are also set to come to a close in June and some will likely be on the move during the summer transfer window.
Here’s a look at those whose futures are uncertain…
9. Kieron Freeman - Swansea
The defender made a shock switch to the Swans less than a month after joining Swindon. He's played just once in the south Wales outfit's push for the top flight. Photo: Joe Pepler
10. Lloyd Isgrove - Bolton
The winger didn't make an appearance during his loan spell at Fratton Park in 2018-19. However, he's hoping for successive League Two promotions, having netted twice in 32 games for Bolton this term. Photo: Joe Pepler
11. Toumani Diagouraga - Morecambe
The midfielder's bagged three times in 38 games during Morecambe's surprise League Two promotion push this campaign. Photo: Joe Pepler
12. Greg Halford - Southend
After being without a club for almost two years, the defender joined the Shrimpers in December. He's scored once in 14 games as Southend look likely to be relegated to non-league this term. Photo: Steve Reid