Traditionally, such a tie would come under the radar for most, with the Blues giving youth the chance to showcase their capabilities.
But after a huge exodus of academy players during the summer, Pompey no longer have the luxury of entrusting participation in this competition entirely on their youngsters.
No doubt, Cowley – who will take charge of the game – will still rely heavily on youth.
But the team is set to be supplemented with senior players who are struggling for first-team.
But who will be those asked to step down and travel to Basingstoke?
Here’s who we think could be involved.
Note: Louis Thompson is unlikely to be involved as tonight’s game is set to be held on the 3G pitch at Winklebury Way.
1. Portsmouth Manager Danny Cowley arrives during the EFL Sky Bet League 1 match between Milton Keynes Dons and Portsmouth at stadium:mk, Milton Keynes, England on 11 September 2021.
Danny Cowley, centre, will be calling upon the services of some of his senior players for tonight's Hampshire Senior Cup game at Basingstoke.
Photo: Jason Brown
2. Alex Bass
The keeper needs game time under his belt - particularly after missing out on an appearance in the Papa John's Trophy defeat at Wimbledon last week because of Covid. He's also featured only seven times since Pompey's 2020-21 season opener at Stevenage in the League Cup. But playing against Basingstoke is no guarantee with teenager Toby Steward someone Danny Cowley is desperate to fast track and see in action at a more senior level.
Picture: Chris Moorhouse
Photo: Chris Moorhouse
3. Connor Ogilvie
The former Gills man appears to be behind Lee Brown in the left-back pecking order after watching the two most recent league games against Wigan and MK Dons from the bench. A Hampshire Senior Cup tie is probably not the type of game he imagined he'd be lining up in when signing for the Blues this summer. Chances are he might be spared the trip to Basingstoke, but it's a possibility Ogilvie will play as he bids to retain his match fitness.
Photo: Daniel Chesterton
4. Paul Downing
The central defender's 90-minute appearance against Wimbledon in the Papa John's Trophy last week represents Downing's only run-out to date this term. He clearly needs match time under his belt and the chance to prove that he should be taken seriously in the battle to form part of the Blues' defensive unit. A strong, commanding performance against the non-league side would be a good starting place to do just that.
Photo: Dennis Goodwin