| 1 | Sat 3 Aug 2019 | 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Sat 17 Aug 2019 | 1-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 3-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 4 | Wed 28 Aug 2019 | 2-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 5 | Sat 31 Aug 2019 | 1-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 6 | Tue 17 Sep 2019 | 2-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 7 | Tue 24 Sep 2019 | 0-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 8 | Tue 22 Oct 2019 | 1-0 v Lincoln CityPortsmouth 1-0 Lincoln City | Sky Bet League One |
| 9 | Sat 26 Oct 2019 | 2-2 v Bristol RoversBristol Rovers 2-2 Portsmouth | Sky Bet League One |
| 10 | Sat 2 Nov 2019 | 1-1 v Oxford UnitedPortsmouth 1-1 Oxford United | Sky Bet League One |
| 11 | Tue 3 Dec 2019 | 2-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 12 | Sat 7 Dec 2019 | 2-2 v Peterborough UnitedPortsmouth 2-2 Peterborough United | Sky Bet League One |
| 13 | Sat 14 Dec 2019 | 1-4 v Accrington StanleyAccrington Stanley 4-1 Portsmouth | Sky Bet League One |
| 14 | Sat 21 Dec 2019 | 1-0 v Ipswich TownPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 15 | Sat 15 Feb 2020 | 2-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 16 | Tue 18 Feb 2020 | 3-2 v Exeter CityPortsmouth 3-2 Exeter City | Leasing.com Trophy Semi Final |
| 17 | Sat 22 Feb 2020 | 0-1 v Fleetwood TownFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 18 | Tue 25 Feb 2020 | 3-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 19 | Mon 2 Mar 2020 | 0-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
| 20 | Sat 7 Mar 2020 | 0-2 v Peterborough UnitedPeterborough United 2-0 Portsmouth | Sky Bet League One |
| 21 | Tue 10 Mar 2020 | 2-2 v Fleetwood TownPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
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