Already, the Blues head coach has recruited 12 new signings in what has been a major squad overhaul.
However, if Cowley is to have his way there will still be more incomings, which could be factored by getting players out of PO4, over the next week.
So, with more anticipated transfer business for Pompey, we posed the question to the Fratton faithful who they’d realistically like to see arrive before the window closes.
And here’s who the Blues supporters on social media want to arrive in the coming days...
1. Sam Greenwood (Leeds)
Joined Leeds from Arsenal Academy on a three-year deal last August. The forward, 19, has mainly operated in the under-23s set up at Elland Road but did feature for Marcelo Bielsa's first-team in pre-season. Leeds could look to offload on loan to gain minutes at senior level Photo: George Wood
2. Liam Delap (Manchester City)
A loan move for the son of former Stoke long throw specialist Rory Delap looks unlikely. Rumoured to be host of Championship clubs keen on short-term deal but City chief Pep Guardiola plans to keep the 18-year-old striker at the Etihad this term Photo: Naomi Baker
3. Dan Crowley (free agent)
Midfielder remains without a club after leaving Birmingham this summer. Has spent time on trial at Pompey's League One rivals Cheltenham and Gillingham. Former Arsenal youth product made 23 appearances on loan at Hull last term as they won promotion to the Championship Photo: Pete Norton
4. Dion Charles (Accrington)
Striker smashed 20 goals in 52 Accy appearances last term. Reports suggest the Northern Ireland international has entered talks over a move to Bristol City, with fellow Championship sides Notts Forest and Barnsley supposedly keen Photo: Pete Norton