| 1 | Sat 5 Aug | 16 1-1 v Bristol RoversPortsmouth 1-1 Bristol Rovers | Sky Bet League One |
| 2 | Tue 15 Aug | 161-0 v Exeter CityPortsmouth 1-0 Exeter City | Sky Bet League One |
| 3 | Sat 19 Aug | 160-0 v Cheltenham TownPortsmouth 0-0 Cheltenham Town | Sky Bet League One |
| 4 | Sat 26 Aug | 160-0 v StevenageStevenage 0-0 Portsmouth | Sky Bet League One |
| 5 | Tue 29 Aug | 161-1 v Peterborough UnitedPortsmouth 1-1 Peterborough United | Carabao Cup Second Round |
| 6 | Sat 2 Sep | 16 3-1 v Peterborough UnitedPortsmouth 3-1 Peterborough United | Sky Bet League One |
| 7 | Tue 19 Sep | 163-2 v BarnsleyBarnsley 2-3 Portsmouth | Sky Bet League One |
| 8 | Sat 23 Sep | 16 2-1 v Lincoln CityPortsmouth 2-1 Lincoln City | Sky Bet League One |
| 9 | Sat 30 Sep | 16 2-1 v Wigan AthleticWigan Athletic 1-2 Portsmouth | Sky Bet League One |
| 10 | Tue 3 Oct | 162-1 v Wycombe WanderersPortsmouth 2-1 Wycombe Wanderers | Sky Bet League One |
| 11 | Sat 7 Oct | 162-0 v Port ValePortsmouth 2-0 Port Vale | Sky Bet League One |
| 12 | Tue 10 Oct | 165-1 v GillinghamPortsmouth 5-1 Gillingham | EFL Trophy |
| 13 | Sat 21 Oct | 161-0 v Carlisle UnitedPortsmouth 1-0 Carlisle United | Sky Bet League One |
| 14 | Tue 24 Oct | 16 0-0 v Cambridge UnitedCambridge United 0-0 Portsmouth | Sky Bet League One |
| 15 | Sat 28 Oct | 163-2 v ReadingReading 2-3 Portsmouth | Sky Bet League One |
| 16 | Sun 5 Nov | 160-1 v ChesterfieldChesterfield 1-0 Portsmouth | Emirates FA Cup First Round |
| 17 | Sat 11 Nov | 162-2 v Charlton AthleticPortsmouth 2-2 Charlton Athletic | Sky Bet League One |
| 18 | Sat 25 Nov | 16 0-4 v BlackpoolPortsmouth 0-4 Blackpool | Sky Bet League One |
| 19 | Mon 11 Dec | 162-0 v Bolton WanderersPortsmouth 2-0 Bolton Wanderers | Sky Bet League One |
| 20 | Sat 16 Dec | 16 3-0 v Shrewsbury TownShrewsbury Town 0-3 Portsmouth | Sky Bet League One |
| 21 | Sat 23 Dec | 161-1 v Fleetwood TownPortsmouth 1-1 Fleetwood Town | Sky Bet League One |
| 22 | Tue 26 Dec | 16 1-2 v Bristol RoversBristol Rovers 2-1 Portsmouth | Sky Bet League One |
| 23 | Fri 29 Dec | 160-0 v Exeter CityExeter City 0-0 Portsmouth | Sky Bet League One |
| 24 | Mon 1 Jan | 162-1 v StevenagePortsmouth 2-1 Stevenage | Sky Bet League One |
| 25 | Sat 6 Jan | 161-2 v Cheltenham TownCheltenham Town 2-1 Portsmouth | Sky Bet League One |
| 26 | Sat 13 Jan | 160-3 v Leyton OrientPortsmouth 0-3 Leyton Orient | Sky Bet League One |
| 27 | Sat 20 Jan | 16 1-0 v Fleetwood TownFleetwood Town 0-1 Portsmouth | Sky Bet League One |
| 28 | Sat 27 Jan | 161-0 v Port ValePort Vale 0-1 Portsmouth | Sky Bet League One |
| 29 | Tue 30 Jan | 162-2 v Oxford UnitedOxford United 2-2 Portsmouth | Sky Bet League One |
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