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…
1. Nathan Thompson - Peterborough
The tough-tackling defender has been a key man for the Posh as they look set for League One automatic promotion. Owner Darragh MacAnthony has admitted Peterborough will offer Thompson a new deal, however. Photo: Nigel Keene
2. Jason Pearce - Charlton
The centre-back has featured 25 times for the Addicks during their League One play-off push. Photo: David Rogers
3. Nathaniel Mendez-Laing - Middlesbrough
The winger was snapped up by Boro in February on a short-term deal after being sacked by Cardiff for cocaine use. Photo: SCC
4. Kyle Bennett - Bristol Rovers
The former Fratton favourite has been out on loan at League Two strugglers Grimsby this season but not played since January. Photo: Joe Pepler