| 1 | Tue 29 Aug | 14 1-1 v Peterborough UnitedPortsmouth 1-1 Peterborough United | Carabao Cup Second Round |
| 2 | Sat 7 Oct | 142-0 v Port ValePortsmouth 2-0 Port Vale | Sky Bet League One |
| 3 | Tue 10 Oct | 145-1 v GillinghamPortsmouth 5-1 Gillingham | EFL Trophy |
| 4 | Tue 7 Nov | 142-1 v Leyton OrientLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 5 | Sat 25 Nov | 140-4 v BlackpoolPortsmouth 0-4 Blackpool | Sky Bet League One |
| 6 | Sat 2 Dec | 143-0 v Northampton TownNorthampton Town 0-3 Portsmouth | Sky Bet League One |
| 7 | Tue 19 Dec | 142-5 v AFC WimbledonPortsmouth 2-5 AFC Wimbledon | EFL Trophy Second Round |
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