| 1 | Sat 3 Aug 2019 | 0-1 v Shrewsbury TownShrewsbury Town 1-0 Portsmouth | Sky Bet League One |
| 2 | Tue 6 Aug 2019 | 3-0 v Birmingham CityPortsmouth 3-0 Birmingham City | Carabao Cup First Round |
| 3 | Sat 10 Aug 2019 | 2-0 v Tranmere RoversPortsmouth 2-0 Tranmere Rovers | Sky Bet League One |
| 4 | Sat 17 Aug 2019 | 1-2 v SunderlandSunderland 2-1 Portsmouth | Sky Bet League One |
| 5 | Tue 20 Aug 2019 | 3-3 v Coventry CityPortsmouth 3-3 Coventry City | Sky Bet League One |
| 6 | Wed 28 Aug 2019 | 2-0 v Queens Park RangersQueens Park Rangers 0-2 Portsmouth | Carabao Cup Second Round |
| 7 | Sat 31 Aug 2019 | 1-1 v BlackpoolBlackpool 1-1 Portsmouth | Sky Bet League One |
| 8 | Tue 3 Sep 2019 | 1-0 v Crawley TownPortsmouth 1-0 Crawley Town | Leasing.com Trophy Southern Group B |
| 9 | Tue 17 Sep 2019 | 2-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 10 | Tue 24 Sep 2019 | 0-4 v SouthamptonPortsmouth 0-4 Southampton | Carabao Cup Third Round |
| 11 | Mon 11 Nov 2019 | 2-1 v Harrogate TownHarrogate Town 1-2 Portsmouth | Emirates FA Cup First Round |
| 12 | Tue 3 Dec 2019 | 2-1 v Northampton TownPortsmouth 2-1 Northampton Town | Leasing.com Trophy Second Round |
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