| 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 |
| 24 | 14/12/2019 | 1-4 v Accrington StanleyAccrington Stanley 4-1 Portsmouth | Sky Bet League One |
| 25 | 21/12/2019 | 1-0 v Ipswich TownPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 26 | 26/12/2019 | 2-0 v Wycombe WanderersPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 27 | 29/12/2019 | 1-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Portsmouth | Sky Bet League One |
| 28 | 1/1/2020 | 1-1 v GillinghamGillingham 1-1 Portsmouth | Sky Bet League One |
| 29 | 11/1/2020 | 2-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 30 | 18/1/2020 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Portsmouth | Sky Bet League One |
| 31 | 21/1/2020 | 2-1 v Scunthorpe UnitedPortsmouth 2-1 Scunthorpe United | Checkatrade Trophy Fourth Round |
| 32 | 25/1/2020 | 4-2 v BarnsleyPortsmouth 4-2 Barnsley | Emirates FA Cup Fourth Round |
| 33 | 28/1/2020 | 2-0 v Lincoln CityLincoln City 0-2 Portsmouth | Sky Bet League One |
| 34 | 1/2/2020 | 2-0 v SunderlandPortsmouth 2-0 Sunderland | Sky Bet League One |
| 35 | 8/2/2020 | 2-0 v Tranmere RoversTranmere Rovers 0-2 Portsmouth | Sky Bet League One |
| 36 | 11/2/2020 | 0-1 v Coventry CityCoventry City 1-0 Portsmouth | Sky Bet League One |
| 37 | 15/2/2020 | 2-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 38 | 18/2/2020 | 3-2 v Exeter CityPortsmouth 3-2 Exeter City | Checkatrade Trophy Semi Final |
| 39 | 22/2/2020 | 0-1 v Fleetwood TownFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 40 | 25/2/2020 | 3-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 41 | 28/2/2020 | 3-0 v RochdalePortsmouth 3-0 Rochdale | Sky Bet League One |
| 42 | 2/3/2020 | 0-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
| 43 | 7/3/2020 | 0-2 v Peterborough UnitedPeterborough United 2-0 Portsmouth | Sky Bet League One |
| 44 | 10/3/2020 | 2-2 v Fleetwood TownPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
