Up to 12 senior members of the current squad could walk away from Fratton Park once the season has finished.
Meanwhile, Pompey have recently changed their transfer policy and will focus on bringing in young, hungry players who still have the best years ahead of them and could potentially be sold for more down the line.
The window will also be Cowley’s third as Blues boss, with the 43-year-old previously stressing the importance of having three attempts to formulate a squad of his ilk.
No market or league will be off limits.
And with Pompey having a history of keeping tabs on games north of the border, we’ve decided to look at what the SPFL has to offer.
Here’s the top under-24 year-olds who could be a realistic target for the Fratton Park outfit in the window.

5. James Penrice - Livingston
Position: Left-back; Age: 23; Appearances: 24; Goals: 0; Assists: 4 Photo: Christian Cooksey

6. Luke McCowan - Dundee
Position: Right-wing; Age: 24; Appearances: 24; Goals: 4; Assists: 1 Photo: Jeff Holmes

7. Callum Slattery - Motherwell
Position: Centre midfield; Age: 23; Appearances: 24; Goals: 1; Assists: 0 Photo: Ian MacNicol

8. Harry Paton - Ross County
Position: Centre midfield; Age: 23; Appearances: 26; Goals: 0; Assists: 3 Photo: Paul Campbell