The Blues head to Isthmian South-Central side Basingstoke Town tomorrow night (7.45pm) in the second round.
Since returning to the competition in recent times, Pompey have primarily fielded sides constructed entirely of Academy players.
However, this season a youthful team will be supplemented by a number of fringe first-team performers.
And Cowley himself will be overseeing the side at Winklebury Way.
He told The News: ‘It’s on a 3G playing surface, so we’ve got to be careful with some.
‘The ones we think we can navigate through safely will play. The ones we don’t think can – or we don’t want to take the risk on - will train.
‘It’s a club game and the Hampshire FA are quite stringent with the rules, which means all players have to be over the age of 16 and you can’t use triallists.
‘Normally this would be an Academy game, but we are not in a position to do that at the moment in terms of numbers.
‘We will try to put a squad together, some of the Academy and some of the first-team players.
‘I will also be taking it. I don’t think it’s right sending the first-team players and then not going myself.’
Since October 2020, Basingstoke have played at Winklebury rather than their long-standing Camrose home.
They were kicked out of The Camrose in summer 2019 and initially played home games at Winchester.
Former owner Rafi Razzak is attempting to redevelop the land on which the ground stands, earmarking a care home and flats.
However, campaigners have successfully managed to list Basingstoke’s former home as an Asset of Community Value – although Razzak is appealing.
In the meantime, they have agreed to lease Winklebury, and drew 2-2 with Chalfont St Peter on Saturday in front of 298 in their most recent home fixture.
Basingstoke are presently third in the Isthmian South-Central league.
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