| 1 | Sat 5 Aug | 5 1-1 v Bristol RoversPortsmouth 1-1 Bristol Rovers | Sky Bet League One |
| 2 | Tue 15 Aug | 5 1-0 v Exeter CityPortsmouth 1-0 Exeter City | Sky Bet League One |
| 3 | Sat 19 Aug | 50-0 v Cheltenham TownPortsmouth 0-0 Cheltenham Town | Sky Bet League One |
| 4 | Sat 26 Aug | 50-0 v StevenageStevenage 0-0 Portsmouth | Sky Bet League One |
| 5 | Tue 29 Aug | 51-1 v Peterborough UnitedPortsmouth 1-1 Peterborough United | Carabao Cup Second Round |
| 6 | Sat 2 Sep | 5 3-1 v Peterborough UnitedPortsmouth 3-1 Peterborough United | Sky Bet League One |
| 7 | Sat 16 Sep | 5 1-1 v Derby CountyDerby County 1-1 Portsmouth | Sky Bet League One |
| 8 | Tue 19 Sep | 53-2 v BarnsleyBarnsley 2-3 Portsmouth | Sky Bet League One |
| 9 | Sat 23 Sep | 52-1 v Lincoln CityPortsmouth 2-1 Lincoln City | Sky Bet League One |
| 10 | Sat 30 Sep | 52-1 v Wigan AthleticWigan Athletic 1-2 Portsmouth | Sky Bet League One |
| 11 | Tue 3 Oct | 5 2-1 v Wycombe WanderersPortsmouth 2-1 Wycombe Wanderers | Sky Bet League One |
| 12 | Wed 11 Oct | 18 4-0 v GibraltarWales 4-0 Gibraltar | International Friendly |
| 13 | Sat 21 Oct | 51-0 v Carlisle UnitedPortsmouth 1-0 Carlisle United | Sky Bet League One |
| 14 | Tue 24 Oct | 50-0 v Cambridge UnitedCambridge United 0-0 Portsmouth | Sky Bet League One |
| 15 | Sat 28 Oct | 53-2 v ReadingReading 2-3 Portsmouth | Sky Bet League One |
| 16 | Sun 5 Nov | 50-1 v ChesterfieldChesterfield 1-0 Portsmouth | Emirates FA Cup First Round |
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