| 1 | Sat 3 Aug 2019 | 30-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Tue 6 Aug 2019 | 33-0 v Birmingham CityPortsmouth 3-0 Birmingham City | Carabao Cup First Round |
| 3 | Sat 10 Aug 2019 | 32-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 4 | Sat 17 Aug 2019 | 31-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 33-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 6 | Sat 5 Oct 2019 | 32-1 v Doncaster RoversDoncaster Rovers 1-2 Portsmouth | Sky Bet League One |
| 7 | Sat 12 Oct 2019 | 3 0-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 8 | Sat 19 Oct 2019 | 3 0-1 v AFC WimbledonAFC Wimbledon 1-0 Portsmouth | Sky Bet League One |
| 9 | Tue 22 Oct 2019 | 31-0 v Lincoln CityPortsmouth 1-0 Lincoln City | Sky Bet League One |
| 10 | Sat 26 Oct 2019 | 32-2 v Bristol RoversBristol Rovers 2-2 Portsmouth | Sky Bet League One |
| 11 | Sat 2 Nov 2019 | 31-1 v Oxford UnitedPortsmouth 1-1 Oxford United | Sky Bet League One |
| 12 | Mon 11 Nov 2019 | 32-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 13 | Sat 23 Nov 2019 | 33-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 14 | Tue 26 Nov 2019 | 33-2 v Rotherham UnitedPortsmouth 3-2 Rotherham United | Sky Bet League One |
| 15 | Sat 7 Dec 2019 | 3 2-2 v Peterborough UnitedPortsmouth 2-2 Peterborough United | Sky Bet League One |
| 16 | Tue 25 Feb 2020 | 33-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 17 | Fri 28 Feb 2020 | 33-0 v RochdalePortsmouth 3-0 Rochdale | Sky Bet League One |
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