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...
Free agents are always viable options to bring in for any side in the lower leagues.
9. Kyle Knoyle
The defender was ever-present in Cambridge's promotion-winning campaign. It's the second time he's escaped the fourth tier, having also done so with Swindon the previous campaign.
Photo: Lewis Storey
10. Abo Eisa
The brother of Peterborough striker, Mo Eisa, has been let go by Scunthorpe but does have potential.
Photo: George Wood
11. Ben Stevenson
The midfielder earned a move to Wolves for an undisclosed fee after breaking through from Coventry earlier in his career. Still has time to meet his potential aged 24 and is yet to sign a new deal at Colchester.
Photo: Alex Pantling
12. Lloyd Isgrove
Surely he wouldn't return?! The winger didn't make a single appearance during his loan spell at Pompey in 2018-19. However, in the poast two seasons, he's won promotion from the third tier with Swindon and Bolton.
Photo: Steve Bardens