| 1 | Sat 4 Aug 2018 | 21-0 v Luton TownPortsmouth 1-0 Luton Town | Sky Bet League One |
| 2 | Sat 11 Aug 2018 | 22-1 v BlackpoolBlackpool 1-2 Portsmouth | Sky Bet League One |
| 3 | Tue 14 Aug 2018 | 21-2 v AFC WimbledonPortsmouth 1-2 AFC Wimbledon | Carabao Cup First Round |
| 4 | Sat 18 Aug 2018 | 24-1 v Oxford UnitedPortsmouth 4-1 Oxford United | Sky Bet League One |
| 5 | Tue 21 Aug 2018 | 22-1 v Bristol RoversBristol Rovers 1-2 Portsmouth | Sky Bet League One |
| 6 | Sat 25 Aug 2018 | 20-0 v Doncaster RoversDoncaster Rovers 0-0 Portsmouth | Sky Bet League One |
| 7 | Sat 1 Sep 2018 | 23-0 v Plymouth ArgylePortsmouth 3-0 Plymouth Argyle | Sky Bet League One |
| 8 | Tue 9 Oct 2018 | 21-0 v Crawley TownCrawley Town 0-1 Portsmouth | Checkatrade Trophy Southern Group A |
| 9 | Sat 13 Oct 2018 | 22-1 v AFC WimbledonAFC Wimbledon 1-2 Portsmouth | Sky Bet League One |
| 10 | Tue 23 Oct 2018 | 22-2 v Burton AlbionPortsmouth 2-2 Burton Albion | Sky Bet League One |
| 11 | Sat 3 Nov 2018 | 21-0 v Bradford CityBradford City 0-1 Portsmouth | Sky Bet League One |
| 12 | Sat 15 Dec 2018 | 21-1 v BarnsleyBarnsley 1-1 Portsmouth | Sky Bet League One |
| 13 | Sat 29 Dec 2018 | 25-2 v Fleetwood TownFleetwood Town 2-5 Portsmouth | Sky Bet League One |
| 14 | Tue 1 Jan 2019 | 22-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 15 | Sat 5 Jan 2019 | 21-0 v Norwich CityNorwich City 0-1 Portsmouth | Emirates FA Cup Third Round |
| 16 | Sat 12 Jan 2019 | 20-1 v BlackpoolPortsmouth 0-1 Blackpool | Sky Bet League One |
| 17 | Sat 19 Jan 2019 | 21-2 v Oxford UnitedOxford United 2-1 Portsmouth | Sky Bet League One |
| 18 | Tue 22 Jan 2019 | 21-0 v Peterborough UnitedPortsmouth 1-0 Peterborough United | Checkatrade Trophy Fourth Round |
| 19 | Sat 26 Jan 2019 | 21-1 v Queens Park RangersPortsmouth 1-1 Queens Park Rangers | Emirates FA Cup Fourth Round |
| 20 | Tue 29 Jan 2019 | 22-3 v Luton TownLuton Town 3-2 Portsmouth | Sky Bet League One |
| 21 | Tue 5 Feb 2019 | 20-2 v Queens Park RangersQueens Park Rangers 2-0 Portsmouth | Emirates FA Cup Fourth Round |
| 22 | Sat 16 Feb 2019 | 2 3-3 v Southend UnitedSouthend United 3-3 Portsmouth | Sky Bet League One |
| 23 | Tue 19 Feb 2019 | 21-1 v Bristol RoversPortsmouth 1-1 Bristol Rovers | Sky Bet League One |
| 24 | Sat 23 Feb 2019 | 20-0 v BarnsleyPortsmouth 0-0 Barnsley | Sky Bet League One |
| 25 | Tue 26 Feb 2019 | 23-0 v BuryBury 0-3 Portsmouth | Checkatrade Trophy Semi Final |
| 26 | Sat 2 Mar 2019 | 25-1 v Bradford CityPortsmouth 5-1 Bradford City | Sky Bet League One |
| 27 | Tue 12 Mar 2019 | 23-2 v WalsallWalsall 2-3 Portsmouth | Sky Bet League One |
| 28 | Sat 23 Mar 2019 | 22-0 v Shrewsbury TownShrewsbury Town 0-2 Portsmouth | Sky Bet League One |
| 29 | Sun 31 Mar 2019 | 22-2 v SunderlandPortsmouth 2-2 Sunderland | Checkatrade Trophy Final |
| 30 | Sat 6 Apr 2019 | 23-2 v Wycombe WanderersWycombe Wanderers 2-3 Portsmouth | Sky Bet League One |
| 31 | Mon 22 Apr 2019 | 22-1 v Coventry CityPortsmouth 2-1 Coventry City | Sky Bet League One |
| 32 | Sat 4 May 2019 | 21-1 v Accrington StanleyPortsmouth 1-1 Accrington Stanley | Sky Bet League One |
| 33 | Sat 11 May 2019 | 20-1 v SunderlandSunderland 1-0 Portsmouth | Sky Bet League One Play-off Semi Final |
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