The Blues currently boast 10 players under the age of 21 and the manager wants to give them all a pathway to establish themselves at Fratton Park.
Not all will be used tonight. However, a select few will be handed the chance to show what they can do and highlight the development they’ve made since returning to training at the end of June.
New-boys Owen Dale and Tom Lowery are also expected to feature, but will they start?Here’s how we think Pompey could line up tonight for the first-round game at the Cardiff City Stadium.
5. Denver Hume - left-back
The left-back hasn't featured for Pompey since mid-March because of a back injury. He's slowly making a recovery and is back training. Could tonight be his comeback appearance? Photo: NatinalWorld
6. Marlon Pack - centre midfield 1
The midfielder has already proven to be a quality bit of business for Pompey this summer - and he'll no doubt want to show Cardiff what they're missing with a swift return to his former Stomping ground. Photo: NationalWorld
7. Jay Mingi - centre midfield 2
The former Charlton and West Ham youngster is yet to start a game for the Blues. That could change tonight, though, after an impressive pre-season and obvious progress made following his return to the club from a non-league loan in January. Photo: NationalWorld
8. Owen Dale - right-wing
The winger only arrived on the south coast on Sunday and trained with his new team-mates for the first time on Monday. But the chances are he'll be handed a starting role as the Blues look to get him up to speed as Marcus Harness' replacement. Photo: NationalWorld