| 1 | Sat 3 Aug 2019 | 8 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 82-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 83-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 4 | Tue 17 Sep 2019 | 82-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 5 | Sat 21 Sep 2019 | 8 0-1 v Wycombe WanderersWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 6 | Tue 24 Sep 2019 | 8 0-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 7 | Sat 28 Sep 2019 | 81-0 v Bolton WanderersPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 8 | Sat 5 Oct 2019 | 82-1 v Doncaster RoversDoncaster Rovers 1-2 Portsmouth | Sky Bet League One |
| 9 | Sat 12 Oct 2019 | 80-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 10 | Sat 23 Nov 2019 | 83-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 11 | Tue 3 Dec 2019 | 82-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 12 | Sat 14 Dec 2019 | 81-4 v Accrington StanleyAccrington Stanley 4-1 Portsmouth | Sky Bet League One |
| 13 | Sun 29 Dec 2019 | 81-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Portsmouth | Sky Bet League One |
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