Including the five loanees, 18 players see their commitments to the Blues at an end.
Of course, there could also be movement in the January window on both temporary and permanent additions as Danny Cowley rehapes his squad.
We’ve assessed how things stand with those players whose deals are due to come to a close.
5. Owen Dale
Plenty of talk about the winger’s situation. Michael Appleton aired the possibility of a January recall, but Pompey hopeful he’ll stay for the season. Beyond that, he has a year to run on his Blackpool deal where a permanent exit isn't unrealistic. Photo: Simon Roe
6. Dan Gifford
Young striker is learning his trade after being handed a third-year scholarship. Spent time at Weymouth and is now with Bognor after a move to Hampton & Richmond fell through. Out to prove he’s worth a pro deal over the rest of the season. Photo: Simon Davies
7. Josh Oluwayemi
The 21-year-old is learning his trade after joining from Spurs and has shown promise. No reason he couldn’t continue to do so at Fratton with a new deal next term. Photo: Simon Davies
8. Joe Pigott
No recall for the Ipswich striker in the parent club’s favour this January. The lack of playing time seems to make it a stretch he could be here beyond the end of the campaign. Photo: Jason Brown