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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1. November 1st - Cowley wanting a new centre-back
‘The fact that we haven’t had Clark available through a long-term injury and Paul Downing fit means we are looking for another centre-half.
‘We want to be competitive in every area and the problem is, in a relatively balanced squad, we’re just lacking in a couple of key areas.
‘Another centre-half would give us flexibility and we would like to be able to add to that position if we could.’ Photo: Jason Brown
2. November 23rd - Interest in Marcus Harness
‘There is no pressure at all from the owners to sell any of our best players – and they have said that from the moment we came in. ‘I would think there will be interest in Marcus in January, unless the football world is blind, which I don’t think it is.
‘He’s a top player, a top, top player. Only Marcus controls his destiny, he can be whatever he wants to be.
‘He obviously has an option on that contract and I am 99.9 percent sure that, at some stage, the option is going to be taken up.’ Photo: Stephen Flynn
3. November 26th - Scouting in Europe
‘We’ve been watching a lot of football in Belgium, which is a good market, we’re looking in Ireland, Scotland and Holland.
‘You have to be realistic and make sure, first and foremost, the players are affordable.
‘Then you have to make sure the players are good enough. That’s what you’re trying to do.
‘There’s definitely more risk when you go abroad, because there’s more variables which can affect the outcome of the signing.’ Photo: LAURIE DIEFFEMBACQ
4. December 1st - Kyle Wootton interest
'We watch a lot of National League and National North and South, it’s our job to try to find one that maybe people aren’t aware of.
‘In an ideal world, we’d like a long-term project that we could sign in January for the number nine position.
‘But I think we might have to make a short-term decision to buy ourselves a bit more time until the summer.
’It’s very hard to find the quality of a forward on a free transfer that has the capabilities and competencies to be successful at Pompey.’ Photo: Steve Flynn/AHPIX LTD