| 1 | Sat 3 Aug 2019 | 26 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Sat 17 Aug 2019 | 261-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 3 | Tue 20 Aug 2019 | 263-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 4 | Wed 28 Aug 2019 | 262-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 5 | Sat 31 Aug 2019 | 261-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 6 | Tue 3 Sep 2019 | 261-0 v Crawley TownPortsmouth 1-0 Crawley Town | Leasing.com Trophy Southern Group B |
| 7 | Tue 17 Sep 2019 | 262-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 8 | Tue 24 Sep 2019 | 260-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 9 | Sat 28 Sep 2019 | 261-0 v Bolton WanderersPortsmouth 1-0 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 5 Oct 2019 | 262-1 v Doncaster RoversDoncaster Rovers 1-2 Portsmouth | Sky Bet League One |
| 11 | Sat 12 Oct 2019 | 260-0 v GillinghamPortsmouth 0-0 Gillingham | Sky Bet League One |
| 12 | Sat 19 Oct 2019 | 260-1 v AFC WimbledonAFC Wimbledon 1-0 Portsmouth | Sky Bet League One |
| 13 | Tue 22 Oct 2019 | 261-0 v Lincoln CityPortsmouth 1-0 Lincoln City | Sky Bet League One |
| 14 | Sat 26 Oct 2019 | 262-2 v Bristol RoversBristol Rovers 2-2 Portsmouth | Sky Bet League One |
| 15 | Sat 2 Nov 2019 | 261-1 v Oxford UnitedPortsmouth 1-1 Oxford United | Sky Bet League One |
| 16 | Mon 11 Nov 2019 | 262-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 17 | Tue 3 Dec 2019 | 262-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
| 18 | Sat 21 Dec 2019 | 261-0 v Ipswich TownPortsmouth 1-0 Ipswich Town | Sky Bet League One |
| 19 | Thu 26 Dec 2019 | 262-0 v Wycombe WanderersPortsmouth 2-0 Wycombe Wanderers | Sky Bet League One |
| 20 | Sun 29 Dec 2019 | 261-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Portsmouth | Sky Bet League One |
| 21 | Wed 1 Jan 2020 | 26 1-1 v GillinghamGillingham 1-1 Portsmouth | Sky Bet League One |
| 22 | Tue 21 Jan 2020 | 262-1 v Scunthorpe UnitedPortsmouth 2-1 Scunthorpe United | Leasing.com Trophy Fourth Round |
| 23 | Sat 25 Jan 2020 | 264-2 v BarnsleyPortsmouth 4-2 Barnsley | Emirates FA Cup Fourth Round |
| 24 | Sat 15 Feb 2020 | 262-0 v Shrewsbury TownPortsmouth 2-0 Shrewsbury Town | Sky Bet League One |
| 25 | Mon 2 Mar 2020 | 260-2 v ArsenalPortsmouth 0-2 Arsenal | Emirates FA Cup Fifth Round |
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