| 1 | 3/8/2019 | 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | 6/8/2019 | 3-0 v Birmingham CityPortsmouth 3-0 Birmingham City | Carabao Cup First Round |
| 3 | 10/8/2019 | 2-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 4 | 17/8/2019 | 1-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 5 | 20/8/2019 | 3-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 6 | 28/8/2019 | 2-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 7 | 31/8/2019 | 1-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 8 | 3/9/2019 | 1-0 v Crawley TownPortsmouth 1-0 Crawley Town | Checkatrade Trophy Southern Group B |
| 9 | 17/9/2019 | 2-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 10 | 21/9/2019 | 0-1 v Wycombe WanderersWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 11 | 24/9/2019 | 0-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 12 | 28/9/2019 | 1-0 v Bolton WanderersPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 13 | 5/10/2019 | 2-1 v Doncaster RoversDoncaster Rovers 1-2 Portsmouth | Sky Bet League One |
| 14 | 12/10/2019 | 0-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 15 | 19/10/2019 | 0-1 v AFC WimbledonAFC Wimbledon 1-0 Portsmouth | Sky Bet League One |
| 16 | 22/10/2019 | 1-0 v Lincoln CityPortsmouth 1-0 Lincoln City | Sky Bet League One |
| 17 | 26/10/2019 | 2-2 v Bristol RoversBristol Rovers 2-2 Portsmouth | Sky Bet League One |
| 18 | 2/11/2019 | 1-1 v Oxford UnitedPortsmouth 1-1 Oxford United | Sky Bet League One |
| 19 | 11/11/2019 | 2-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 20 | 23/11/2019 | 3-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 21 | 26/11/2019 | 3-2 v Rotherham UnitedPortsmouth 3-2 Rotherham United | Sky Bet League One |
| 22 | 3/12/2019 | 2-1 v Northampton TownPortsmouth 2-1 Northampton Town | Checkatrade Trophy Second Round |
| 23 | 7/12/2019 | 2-2 v Peterborough UnitedPortsmouth 2-2 Peterborough United | Sky Bet League One |
