And D-Day is approaching for John Mousinho to make his final decision on the futures of the likes of Clark Robertson, Connor Ogilvie and Louis Thompson.
The Blues are expected to have another squad rebuild after another failed season has seen them miss out on promotion from League One.
But what are the contract situations of players from clubs elsewhere in the division?
Using Transfermarkt, we’ve taken a look at the sides with the most men without a deal beyond this season in the third tier to see where Pompey rank.
Here’s what we found.
. The League One sides with the most amount of out-of-contract players
The League One sides with the most amount of out-of-contract players. Photo: Jason Brown
. Peterborough - 2
Out-of-contract players: Nathan Thompson, Joe Ward. Photo: Catherine Ivill
. Oxford United - 2
Out-of-contract players: Djavan Anderson, Yanic Wildschut. Photo: Richard Heathcote
. Fleetwood - 3
Out-of-contract players: Daniel Batty, Harrison Holgate, Darnell Johnson. Photo: Pete Norton
. Lincoln - 5
Out-of-contract players: Sean Roughan, Adam Jackson, Max Sanders, Joe Walsh, Charles Vernam. Photo: Bryn Lennon
. Barnsley - 5
Out-of-contract players: Luke Thomas, Clarke Oduor, James Norwood, Jordan Helliwell, Aiden Marsh. Photo: Michael Regan
. Wycombe - 5
Out-of-contract players: Jordan Obita, Jack Wakely, Nick Freeman, Jordan Willis, Tjay De Barr. Photo: Pete Norton
. MK Dons - 5
Out-of-contract players: Sullay Kaikai, Zak Jules, Tennai Watson, Dean Lewington, Brooklyn Ilunga. Photo: Pete Norton
. Ipswich - 6
Out-of-contract players: Massimo Luongo, Joel Coleman, Sone Aluko, Richard Keogh, Kane Vincent-Young, Nick Hayes. Photo: Alex Davidson
1. The League One sides with the most amount of out-of-contract players
The League One sides with the most amount of out-of-contract players. Photo: Jason Brown
2. Peterborough - 2
Out-of-contract players: Nathan Thompson, Joe Ward. Photo: Catherine Ivill
3. Oxford United - 2
Out-of-contract players: Djavan Anderson, Yanic Wildschut. Photo: Richard Heathcote
4. Fleetwood - 3
Out-of-contract players: Daniel Batty, Harrison Holgate, Darnell Johnson. Photo: Pete Norton