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.
No doubt, Cowley – who will take charge of the game – will still rely heavily on youth.