| 1 | Sat 9 Aug | 51-0 v Oxford UnitedOxford United 0-1 Portsmouth | Sky Bet Championship |
| 2 | Tue 12 Aug | 5 1-2 v ReadingPortsmouth 1-2 Reading | Carabao Cup First Round |
| 3 | Sat 16 Aug | 5 1-2 v Norwich CityPortsmouth 1-2 Norwich City | Sky Bet Championship |
| 4 | Sat 23 Aug | 5 1-1 v West Bromwich AlbionWest Bromwich Albion 1-1 Portsmouth | Sky Bet Championship |
| 5 | Sat 30 Aug | 51-0 v Preston North EndPortsmouth 1-0 Preston North End | Sky Bet Championship |
| 6 | Sun 14 Sep | 50-0 v SouthamptonSouthampton 0-0 Portsmouth | Sky Bet Championship |
| 7 | Sat 20 Sep | 50-2 v Sheffield WednesdayPortsmouth 0-2 Sheffield Wednesday | Sky Bet Championship |
| 8 | Sat 27 Sep | 51-2 v Ipswich TownIpswich Town 2-1 Portsmouth | Sky Bet Championship |
| 9 | Wed 1 Oct | 52-2 v WatfordPortsmouth 2-2 Watford | Sky Bet Championship |
| 10 | Sat 4 Oct | 51-0 v MiddlesbroughPortsmouth 1-0 Middlesbrough | Sky Bet Championship |
| 11 | Sat 18 Oct | 51-1 v Leicester CityLeicester City 1-1 Portsmouth | Sky Bet Championship |
| 12 | Tue 21 Oct | 51-2 v Coventry CityPortsmouth 1-2 Coventry City | Sky Bet Championship |
| 13 | Sat 25 Oct | 50-1 v Stoke CityPortsmouth 0-1 Stoke City | Sky Bet Championship |
| 14 | Sat 1 Nov | 50-4 v Birmingham CityBirmingham City 4-0 Portsmouth | Sky Bet Championship |
| 15 | Wed 5 Nov | 50-0 v WrexhamPortsmouth 0-0 Wrexham | Sky Bet Championship |
| 16 | Sat 8 Nov | 52-3 v Hull CityHull City 3-2 Portsmouth | Sky Bet Championship |
| 17 | Sat 22 Nov | 5 3-1 v MillwallPortsmouth 3-1 Millwall | Sky Bet Championship |
| 18 | Wed 26 Nov | 50-3 v Sheffield UnitedSheffield United 3-0 Portsmouth | Sky Bet Championship |
| 19 | Sat 29 Nov | 5 0-1 v Bristol CityPortsmouth 0-1 Bristol City | Sky Bet Championship |
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