| 1 | Sat 3 Aug 2019 | 2 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Tue 6 Aug 2019 | 23-0 v Birmingham CityPortsmouth 3-0 Birmingham City | Carabao Cup First Round |
| 3 | Sat 10 Aug 2019 | 22-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 4 | Sat 17 Aug 2019 | 21-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 5 | Wed 28 Aug 2019 | 22-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 6 | Sat 31 Aug 2019 | 21-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 7 | Mon 11 Nov 2019 | 22-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 8 | Sat 23 Nov 2019 | 23-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 9 | Tue 26 Nov 2019 | 23-2 v Rotherham UnitedPortsmouth 3-2 Rotherham United | Sky Bet League One |
| 10 | Tue 3 Dec 2019 | 22-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 11 | Sat 14 Dec 2019 | 21-4 v Accrington StanleyAccrington Stanley 4-1 Portsmouth | Sky Bet League One |
| 12 | Sat 21 Dec 2019 | 21-0 v Ipswich TownPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 13 | Thu 26 Dec 2019 | 22-0 v Wycombe WanderersPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 14 | Sun 29 Dec 2019 | 21-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Portsmouth | Sky Bet League One |
| 15 | Wed 1 Jan 2020 | 21-1 v GillinghamGillingham 1-1 Portsmouth | Sky Bet League One |
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