Pompey Academy will make the trip to Cray Wanderers in the FA Youth Cup later this month.
Cray defeated Worthing 2-1 last night to move into the second round of the competition and set up a tie with the young Blues.
Pompey reached round three last season before falling to a 2-1 extra-time defeat to Leicester.
The hope is they will at least be able to match that feat this term.
For Cray it’s been a record-breaking run, with the Blues offering a potential huge scalp.
All second-round matches must be played before Saturday, November 17.