| 1 | Tue 6 Aug 2019 | 383-0 v Birmingham CityPortsmouth 3-0 Birmingham City | Carabao Cup First Round |
| 2 | Tue 20 Aug 2019 | 383-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 3 | Wed 28 Aug 2019 | 382-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 4 | Sat 31 Aug 2019 | 38 1-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 5 | Tue 3 Sep 2019 | 381-0 v Crawley TownPortsmouth 1-0 Crawley Town | Leasing.com Trophy Southern Group B |
| 6 | Tue 17 Sep 2019 | 382-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 7 | Sat 21 Sep 2019 | 380-1 v Wycombe WanderersWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 8 | Tue 24 Sep 2019 | 380-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 9 | Sat 28 Sep 2019 | 381-0 v Bolton WanderersPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 10 | Mon 11 Nov 2019 | 382-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 11 | Sat 23 Nov 2019 | 383-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 12 | Tue 26 Nov 2019 | 383-2 v Rotherham UnitedPortsmouth 3-2 Rotherham United | Sky Bet League One |
| 13 | Tue 3 Dec 2019 | 382-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 14 | Sat 7 Dec 2019 | 382-2 v Peterborough UnitedPortsmouth 2-2 Peterborough United | Sky Bet League One |
| 15 | Sat 11 Jan 2020 | 382-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 16 | Tue 21 Jan 2020 | 382-1 v Scunthorpe UnitedPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
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