It will also provide the first opportunity to get a glimpse of the five signings that have so far arrived through the door at Fratton Park this summer.
Because of the nature of pre-season friendlies, it’s unlikely Cowley will name his strongest starting XI for the game at Westleigh Park.
The head coach will no doubt want to look at certain combinations, have a look at players like Reeco Hackett-Fairchild who spent last season on loan at Southend, and even cast an eye over triallists who have been with the Blues since their return to pre-season training last week.
However, that hasn’t stopped up surmising what Pompey’s strongest Xi would look like if Cowley did go down the route of going strong against the Hawks – or if the season were to start this weekend.
Here’s the starting XI we came up with. Feel free to let us know if you agree or not!
From left: Gavin Bazunu, Ryan Tunnicliffe, Clark Robertson and Ronan Curtis
2. Goalkeeper - Gavin Bazunu
The Republic of Ireland international goalkeeper arrived on a season-long loan from Manchester City last week. He'll go head-to-head with Alex Bass for the right to be Pompey's No1 keeper. But with Bazunu featuring 32 times for Rochdale last season and determined to keep hold of his Eire starting place, he's not here to sit on the bench. Picture: Lewis Storey/Getty Images
Photo: Lewis Storey
3. Right-back - Callum Johnson
Pompey have been linked with a host of names so far this summer but none would be classified as right-backs to threaten Johnson's position, which is a huge compliment. There's still time for that to change, though, especially with Haji Mnoga likely to head out on loan this season. A replacement for him will need to be found. Saying that, right-back isn't exactly top of Danny Cowley's priority list this transfer window.
4. Centre-back - Paul Downing
It remains a toss-up at this moment who plays alongside Pompey new-boy Clark Robertson in the centre of defence. Sean Raggett's past history with Danny Cowley, plus his 52 games in all competitions last season, would suggest he's the favourite. But Downing came in to the Pompey starting XI on the final day of the season against Accrington at Raggett's expense. That suggests Cowley might favour Downing over the former Lincoln and Norwich defender. We wait and see!
Photo: Joe Pepler