Last pre-season, high-profile players such as Tom Naylor, Jack Whatmough, Craig MacGillivray, and Ben Close failed to extend their stays at Fratton Park.
With Danny Cowley at the helm for exactly a year, he’ll now have to decide who stays, or who goes for free at the end of the season.
Here’s the latest on each’s future – and who Blues writer Sam Cox believes should be handed new contracts.
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13. Gavin Bazunu - No
This one is out of Pompey's hands. If they fail to reach the Championship, which is looking likely, their chances of securing another loan deal looks unlikely. And they won't be able to afford the finances to make his loan permanent. Photo: The News
14. Hayden Carter - No
Another situation the same as Bazunu's, Carter may be eyeing a Championship berth next season with two-years remaining on his Blackburn deal. May be priced out of making it permanent. Photo: The News
15. Mahlon Romeo - No
Romeo could be eyeing a return to the Championship next season, and Pompey could save funds and invest in a permanent solution at right-back. Photo: The News
16. Tyler Walker - No
Walker's high wages coinciding with his underwhelming performances, Pompey shouldn't pursue him long-term. Wouldn't be surprised, however, to see Cowley back in for him in the summer. Photo: The News