Pompey have been matched against Charlton and Crawley in the Checkatrade Trophy.
The Blues have been placed in southern group A in the much-maligned competition for the 2017-18 season.
Kenny Jackett’s side will also face a category one under-21 - with the draw for that being made Wednesday at 3pm
Brighton, Chelsea, Fulham, Reading, Southampton, Swansea, Tottenham or West Ham are the sides they could be matched with.
The top two sides from the group progress, with penalty shoot-outs after drawn games seeing the winning side receive a bonus point.