Pompey will field a reserve team in three different cup competitions this season.
They are once again taking part in the Premier League Cup, Hampshire Senior Cup and Central League Cup.
The former is primarily for under-23 sides, although clubs can field three overage outfield players and on overage goalkeeper.
Pompey have to negotiate a qualifying round at Doncaster in order to reach the group stage and will be trying to repeat their success of 2017, when they made it all the way to the semi-finals.
A trip to holders Havant & Waterlooville awaits in the Hampshire Senior Cup, with both sides having received a bye through to the second round.
The Central League Cup begins with a group stage format and the Blues have a home fixture against Bournemouth, which will be played at Baffins' PMC Stadium.
They will then have two games on the road at Bristol Rovers and Plymouth.
| Date | Opposition | Comp | KO | Venue |
| Tue, Sep 10 | Doncaster (A) | PLC | 7pm | Keepmoat Stadium |
| Wed, Sep 18 | Hawks (A) | HSC | 7.45pm | Westleigh Park |
| Tue, Oct 1 | Bournemouth (H) | CLC | 7pm | PMC Stadium |
| Tue, Oct 29 | Bristol Rovers (A) | CLC | 2pm | TBC |
| Tue, Nov 26 | Plymouth (A) | CLC | 2pm | TBC |
Please note that dates, times and venues are all subject to change.