| 1 | Tue 3 Sep 2019 | 1-0 v Crawley TownPortsmouth 1-0 Crawley Town | Leasing.com Trophy Southern Group B |
| 2 | Sat 12 Oct 2019 | 0-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 3 | Tue 3 Dec 2019 | 2-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 4 | Wed 1 Jan 2020 | 1-1 v GillinghamGillingham 1-1 Portsmouth | Sky Bet League One |
| 5 | Sat 11 Jan 2020 | 2-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 6 | Sat 18 Jan 2020 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Portsmouth | Sky Bet League One |
| 7 | Sat 25 Jan 2020 | 4-2 v BarnsleyPortsmouth 4-2 Barnsley | Emirates FA Cup Fourth Round |
| 8 | Tue 28 Jan 2020 | 2-0 v Lincoln CityLincoln City 0-2 Portsmouth | Sky Bet League One |
| 9 | Sat 1 Feb 2020 | 2-0 v SunderlandPortsmouth 2-0 Sunderland | Sky Bet League One |
| 10 | Sat 8 Feb 2020 | 2-0 v Tranmere RoversTranmere Rovers 0-2 Portsmouth | Sky Bet League One |
| 11 | Tue 11 Feb 2020 | 0-1 v Coventry CityCoventry City 1-0 Portsmouth | Sky Bet League One |
| 12 | Sat 15 Feb 2020 | 2-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 13 | Tue 18 Feb 2020 | 3-2 v Exeter CityPortsmouth 3-2 Exeter City | Leasing.com Trophy Semi Final |
| 14 | Sat 22 Feb 2020 | 0-1 v Fleetwood TownFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 15 | Tue 25 Feb 2020 | 3-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 16 | Fri 28 Feb 2020 | 3-0 v RochdalePortsmouth 3-0 Rochdale | Sky Bet League One |
| 17 | Mon 2 Mar 2020 | 0-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
| 18 | Sat 7 Mar 2020 | 0-2 v Peterborough UnitedPeterborough United 2-0 Portsmouth | Sky Bet League One |
| 19 | Tue 10 Mar 2020 | 2-2 v Fleetwood TownPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
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