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...
1. Randell Williams
The winger has turned down a new deal at Exeter. Williams reportedly almost made a £500,000 move to Peterborough last summer and has been linked with Pompey in the past. Likely to have plenty of suitors. Photo: Harry Trump
2. Ibou Touray
The left-back helped Salford defeat Pompey in the Papa John's Trophy final in March. Touray played 51 times for the Ammies this season and was named in the League Two Team of the Seaon. May want to now step up to the higher level. The Blues need a left-sided defender after Charlie Daniels' departure. Photo: Gareth Copley
3. Carlos Mendes Gomes
The former Athletico Madrid winger has been the talisman of Morecambe's shock promotion push, recording 15 goals and three assists in 43 games. Another who will be in high demand. Photo: Lewis Storey
4. Paul Mullin
The striker plundered a whopping 34 goals in 50 games to lead Cambridge to promotion this season. He's been offered fresh terms but will have options. Photo: Stu Forster