The Blues boss has made it evident throughout the season his desire to bring in new men next month, with a striker and a central defender at the top of the list.
Incomings and outgoings will prove to be a challenge with limited funds to spend, while also deciding which loan men to send back.
So what clues has Cowley given us to how he will go about his business?
We’ve trawled through our archive to see what we can learn about how the Pompey head coach will go about his recruitment work.
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So what clues has Cowley given us to how he will go about his business?