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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9. Jayden Reid - Yes
Reid hasn't been seen since preseason after injuring his knee in a friendly. The club do have the option to extend by a year and should do so for him to complete his rehab and become an option next season. Picture: Portsmouth FC Photo: Portsmouth FC
10. Jay Mingi - Yes
Although the Blues don't have a clause to extend his current deal, they should offer him fresh terms. This would then give them the option to keep or sell on their own terms after National League Wrexham had announced their interest in the midfielder in January. Could be a way to raise funds. Picture: Portsmouth FC Photo: Portsmouth FC
11. Aiden O'Brien - Yes
One of the most obvious decisions the club could make in the summer. O'Brien has settled well at Fratton Park following his deadline day move from Sunderland, and looks a real asset in League One. Picture: Portsmouth FC Photo: Portsmouth FC
12. Ollie Webber - Yes
With Gavin Bazunu set to return to Manchester City in the summer, the number one spot is up for grabs. Webber's future will be decided on his performances in training as it's unlikely he'll knock the Premier League loanee out of the side. Picture: Portsmouth FC Photo: Portsmouth FC