| 1 | Sat 3 Aug 2019 | 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Sat 10 Aug 2019 | 2-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 3 | Sat 17 Aug 2019 | 1-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 4 | Tue 20 Aug 2019 | 3-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 5 | Wed 28 Aug 2019 | 2-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 6 | Sat 31 Aug 2019 | 1-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 7 | Tue 3 Sep 2019 | 1-0 v Crawley TownPortsmouth 1-0 Crawley Town | Leasing.com Trophy Southern Group B |
| 8 | Tue 17 Sep 2019 | 2-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 9 | Sat 21 Sep 2019 | 0-1 v Wycombe WanderersWycombe Wanderers 1-0 Portsmouth | Sky Bet League One |
| 10 | Tue 24 Sep 2019 | 0-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 11 | Sat 28 Sep 2019 | 1-0 v Bolton WanderersPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 12 | Sat 5 Oct 2019 | 2-1 v Doncaster RoversDoncaster Rovers 1-2 Portsmouth | Sky Bet League One |
| 13 | Sat 12 Oct 2019 | 0-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 14 | Sat 19 Oct 2019 | 0-1 v AFC WimbledonAFC Wimbledon 1-0 Portsmouth | Sky Bet League One |
| 15 | Tue 22 Oct 2019 | 1-0 v Lincoln CityPortsmouth 1-0 Lincoln City | Sky Bet League One |
| 16 | Sat 26 Oct 2019 | 2-2 v Bristol RoversBristol Rovers 2-2 Portsmouth | Sky Bet League One |
| 17 | Sat 2 Nov 2019 | 1-1 v Oxford UnitedPortsmouth 1-1 Oxford United | Sky Bet League One |
| 18 | Mon 11 Nov 2019 | 2-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 19 | Sat 23 Nov 2019 | 3-0 v RochdaleRochdale 0-3 Portsmouth | Sky Bet League One |
| 20 | Tue 26 Nov 2019 | 3-2 v Rotherham UnitedPortsmouth 3-2 Rotherham United | Sky Bet League One |
| 21 | Tue 3 Dec 2019 | 2-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 22 | Sat 7 Dec 2019 | 2-2 v Peterborough UnitedPortsmouth 2-2 Peterborough United | Sky Bet League One |
| 23 | Sat 14 Dec 2019 | 1-4 v Accrington StanleyAccrington Stanley 4-1 Portsmouth | Sky Bet League One |
| 24 | Thu 26 Dec 2019 | 2-0 v Wycombe WanderersPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 25 | Sun 29 Dec 2019 | 1-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Portsmouth | Sky Bet League One |
| 26 | Wed 1 Jan 2020 | 1-1 v GillinghamGillingham 1-1 Portsmouth | Sky Bet League One |
| 27 | Sat 11 Jan 2020 | 2-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 28 | Sat 18 Jan 2020 | 1-0 v Bolton WanderersBolton Wanderers 0-1 Portsmouth | Sky Bet League One |
| 29 | Tue 21 Jan 2020 | 2-1 v Scunthorpe UnitedPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
| 30 | Sat 25 Jan 2020 | 4-2 v BarnsleyPortsmouth 4-2 Barnsley | Emirates FA Cup Fourth Round |
| 31 | Tue 28 Jan 2020 | 2-0 v Lincoln CityLincoln City 0-2 Portsmouth | Sky Bet League One |
| 32 | Sat 1 Feb 2020 | 2-0 v SunderlandPortsmouth 2-0 Sunderland | Sky Bet League One |
| 33 | Tue 11 Feb 2020 | 0-1 v Coventry CityCoventry City 1-0 Portsmouth | Sky Bet League One |
| 34 | Sat 15 Feb 2020 | 2-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 35 | Tue 18 Feb 2020 | 3-2 v Exeter CityPortsmouth 3-2 Exeter City | Leasing.com Trophy Semi Final |
| 36 | Sat 22 Feb 2020 | 0-1 v Fleetwood TownFleetwood Town 1-0 Portsmouth | Sky Bet League One |
| 37 | Tue 25 Feb 2020 | 3-1 v Milton Keynes DonsPortsmouth 3-1 Milton Keynes Dons | Sky Bet League One |
| 38 | Fri 28 Feb 2020 | 3-0 v RochdalePortsmouth 3-0 Rochdale | Sky Bet League One |
| 39 | Mon 2 Mar 2020 | 0-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
| 40 | Sat 7 Mar 2020 | 0-2 v Peterborough UnitedPeterborough United 2-0 Portsmouth | Sky Bet League One |
| 41 | Tue 10 Mar 2020 | 2-2 v Fleetwood TownPortsmouth 2-2 Fleetwood Town | Sky Bet League One |
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