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.
5. Michael Jacobs
Somehow the attacking midfielder is clearly well down the pecking order at Fratton Park - a fact highlighted by Danny Cowley's decision to play Reeco Hackett-Fairchild instead of Ronan Curtis on the left wing against MK Dons on Saturday. Jacobs grew into last week's Papa John's Trophy defeat at Wimbledon and you get the sense that with minutes under his belt and injuries behind him, his influence will grow. Pompey currently lack creativity - and surely Jacobs needs a chance to show he's the one the Blues can rely on. Photo: Jason Brown
6. Gassan Ahadme
Ahadme's pre-season goal record (8) speaks for itself - hence why the Blues took a punt on him in the summer. Yet he's been unable to replicate that form since the season began and wasn't even on the bench for Pompey's 1-0 defeat at MK Dons on Saturday. A run-out against Basingstoke tonight could help him rediscover his form and send a clear reminder to Cowley that he's got a lot to offer this team. Photo: Daniel Chesterton
7. George Hirst
The on-loan Leicester man has made a favourable impression since arriving at Fratton Park. But he's not at the stage yet where his name is being used in discussions about freshening up Pompey's goal-shy attack. Indeed, like Ahadme, he wasn't even on the bench at Stadium MK on Saturday. A start tonight against Basingstoke and a couple of goals will no doubt propel him back into the conversation. Goals are in short supply at the moment - and Hirst has a huge change to show what he can offer, irrespective of the opposition. Photo: Daniel Chesterton