Pompey Reserves will travel to Doncaster for a group-stage spot in the Premier League Cup.
The Blues meet their fellow League One side in the qualifying round of the competition earmarked for Tuesday, September 10 (7pm).
The likes of Alex Bass and Matt Casey are likely to feature for Jake Wigley's side, while Oli Hawkins and Ryan Williams could also play if they return from injury.
Pompey will be hoping to fare better than they did in the Premier League Cup last term.
They were beaten 3-0 by Plymouth in the qualifying round at Home Park.
The Blues do have fond memories of the tournament, however.
During the 2016-17 season, they reached the semi-finals but fell to a 2-1 extra-time defeat against Swansea.
The reserves will also compete in the Central League Cup.
They'll face AFC Bournemouth, which is provisionally booked for Tuesday, October 1 before travelling to Bristol Rovers (Tuesday, October 29) and Plymouth (Tuesday, November 26).
Pompey have again entered the Hampshire Senior Cup and have been drawn at the Hawks in the second round.
That game has been earmarked to take place the week beginning Monday, September 16.