Pompey will face Norwich under-21s in this season’s Checkatrade Trophy.
The Canaries have been drawn in Southern Section Group B of the competition along with the Blues, Oxford United and Crawley.
And the newly-promoted Premier League side’s youngsters will visit Fratton Park rather than the game taking place at Carrow Road.
Kenny Jackett’s troops defeated Norwich’s first team 1-0 in the FA Cup third round last campaign.
Andre Green's stoppage-time strike ensured Pompey pulled of an upset against a Canaries side that would go on to claim the Championship crown.
Crawley will also visit the south coast, while the Blues have to make the trip up the A34 to League One rivals Oxford.
Fixtures are set to be played in the weeks beginning September 2, October 7 and November 11, although there is some flexibility.
The 48 Football League clubs were placed into pre-determined groups. Consideration to ensure travel time is minimised for supporters was given.
Jackett's troops aim to defend the Checkatrade Trophy following last season’s triumph.
Pompey claimed the silverware after defeating Sunderland via a penalty shootout at Wembley in March, after the high-octane clash ended 2-2 following extra-time.