With only 13 players remaining under contract at Fratton Park, there will be plenty of new faces arriving at the Blues.
Danny Cowley will be looking to maximise his budget to ensure he compiles a squad capable of another League One promotion push.
Free agents are always viable options to bring in for any side in the lower leagues.
This transfer window, they might be more important than ever given the financial impact the Covid-19 pandemic has had on football.
When scouring who is available, Cowley could look to see which players who have starred in League Two this season are available.
They’d offer more value for money and a gem could potentially be unearthed.
Here are a look at a few that could fit the bill...
5. Manny Monthe
Someone who has been on Pompey's wish-list in the past. The centre-back is currently trying to get Tranmere promoted back to League One via the play-offs. Photo: PAUL ELLIS/AFP via Getty Image
6. Dan Happe
The 22-year-old has already made more than 100 outings for Leyton Orient. The Londoners have offered him a new deal but an offer from the third tier would be tempting for the 6ft 5inch centre-back. Photo: Jacques Feeney
7. Otis Khan
The winger has played a prominent role during Tranmere's promotion bid and was linked with Sunderland and Preston earlier this year. Photo: Lewis Storey
8. Jacob Bedeau
The former Aston Villa centre-back has already been linked with Pompey, along with League One rivals MK Dons, Oxford and Fleetwood. He's been released by Scunthorpe because of financial reasons. Photo: George Wood