A young Pompey Reserves side will face Plymouth in the Premier League Cup qualifying round on Tuesday (September 4) evening.
While the first team are in Checkatrade Trophy action at Fratton Park, the second string travel to Home Park (7pm kick-off).
The Blues are trying to reach the group stage of the competition for a third successive season and made it as far as the semi-finals in 2016/17.
Jake Wigley will be in charge for the visitors, with the side likely to be made up of academy players.
Should Pompey make it through, they will compete in Group F with Aston Villa, Bristol City and Derby.
The Premier League Cup is a competition for under-23 sides, although teams can field three overage outfield players and an overage goalkeeper.