Pompey will start the defence of the Checkatrade Trophy against Crawley and Oxford.
The Blues have been drawn in Southern Section Group B in the opening round of the competition.
And Kenny Jackett’s troops will discover which invited under-21 side will also feature in their pool when the draw takes place on Friday (12.15pm).
Pompey met Crawley in the first stage on the way to clinching the silverware last season.
The Blues delivered a 1-0 win at the Broadfield Stadium, with Dion Donohue netting his only goal for the club.
Jackett’s men play a pre-season friendly against the Reds on Saturday, July 27.
In addition, Pompey will do battle with League One rivals Oxford.
They last met in the competition in 2013 when it was an all-knockout format.
Pompey delivered a 2-1 victory, with Patrick Agyemang and John Marquis scoring.
Jackett’s side could be drawn against under-21 sides Arsenal, Brighton, Chelsea, Fulham, Norwich, Southampton, Tottenham and West Ham.