| 1 | Tue 29 Aug | 21-1 v Peterborough UnitedPortsmouth 1-1 Peterborough United | Carabao Cup Second Round |
| 2 | Sat 2 Sep | 23-1 v Peterborough UnitedPortsmouth 3-1 Peterborough United | Sky Bet League One |
| 3 | Sat 16 Sep | 21-1 v Derby CountyDerby County 1-1 Portsmouth | Sky Bet League One |
| 4 | Tue 10 Oct | 25-1 v GillinghamPortsmouth 5-1 Gillingham | EFL Trophy |
| 5 | Tue 24 Oct | 20-0 v Cambridge UnitedCambridge United 0-0 Portsmouth | Sky Bet League One |
| 6 | Sat 28 Oct | 23-2 v ReadingReading 2-3 Portsmouth | Sky Bet League One |
| 7 | Sun 5 Nov | 20-1 v ChesterfieldChesterfield 1-0 Portsmouth | Emirates FA Cup First Round |
| 8 | Tue 7 Nov | 22-1 v Leyton OrientLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 9 | Sat 11 Nov | 22-2 v Charlton AthleticPortsmouth 2-2 Charlton Athletic | Sky Bet League One |
| 10 | Mon 11 Dec | 22-0 v Bolton WanderersPortsmouth 2-0 Bolton Wanderers | Sky Bet League One |
| 11 | Tue 19 Dec | 22-5 v AFC WimbledonPortsmouth 2-5 AFC Wimbledon | EFL Trophy Second Round |
| 12 | Sat 16 Mar | 21-0 v Peterborough UnitedPeterborough United 0-1 Portsmouth | Sky Bet League One |
| 13 | Fri 29 Mar | 23-1 v Wycombe WanderersWycombe Wanderers 1-3 Portsmouth | Sky Bet League One |
| 14 | Sat 6 Apr | 2 3-1 v Shrewsbury TownPortsmouth 3-1 Shrewsbury Town | Sky Bet League One |
| 15 | Tue 16 Apr | 23-2 v BarnsleyPortsmouth 3-2 Barnsley | Sky Bet League One |
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