With 12 players out of contract, it promises to be another busy period of recruitment for the head coach in his second summer at Fratton Park.
And the Blues boss continues to be relentless in his work, as he goes about assembling his list of targets for the months ahead with his recruitment team.
That includes taking in as many games as possible, with there no substitute for putting the miles in and watching action in the flesh in the Pompey boss’ eyes.
With no game for two-and-a-half weeks, that’s given Cowley the chance to do just that along with his small but hard working group of backroom staff.
On Saturday, Sixfields was the 43-year-old’s destination as he watched high-flying Northampton defeat Hartlepool 2-0.
Pompey are known to have been interested in one Cobblers player this season in Ali Koiki.
There was a belief the attacking left-back could’ve moved to Sunderland in January as Denver Hume came to PO4, although a deal never materialised.
With Connor Ogilvie now operating more as a central defender, it could be a position Cowley has eyes on further strengthening this summer.
But he would’ve been disappointed not to have been given the chance to watch Koiki in action, with the former Bristol Rovers man ruled out through a hamstring injury.
There was a Northampton player having an outstanding season on display, however.
Highly-regarded Fraser Horsfall again impressed, with the 25-year-old helping his side to a clean sheet in the 2-0 win.
Despite being a central defender, Horsfall has helped himself to an excellent return of eight goals this season.
With his contract coming to a close, boss Jon Brady recently admitted he may have a job on his hands keeping the former Macclesfield man beyond the summer.
Other players in action were long-serving winger Sam Hoskins who grabbed his ninth goal of the season, and central midfielder Paul Lewis, who has seven goals to his name.
Hartlepool have a number of players out of contract in the summer, including 11-goal striker Luke Molyneux. The ex-Sunderland man is being tipped as a likely Pools player of the season.
Left-sided David Ferguson and former Newcastle United right-back Jamie Sterry have both also impressed for Graeme Lee’s side.
A message from the Editor, Mark Waldron
You can support our local team of expert Pompey writers by subscribing here for all the latest news from Fratton Park for less than 25p per week.