| 1 | Sat 7 Jul 2018 | 62-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Portsmouth | Friendly |
| 2 | Sat 4 Aug 2018 | 61-0 v Luton TownPortsmouth 1-0 Luton Town | Sky Bet League One |
| 3 | Tue 14 Aug 2018 | 61-2 v AFC WimbledonPortsmouth 1-2 AFC Wimbledon | Carabao Cup First Round |
| 4 | Sat 1 Sep 2018 | 63-0 v Plymouth ArgylePortsmouth 3-0 Plymouth Argyle | Sky Bet League One |
| 5 | Tue 4 Sep 2018 | 6 4-0 v GillinghamPortsmouth 4-0 Gillingham | Checkatrade Trophy Southern Group A |
| 6 | Sat 8 Sep 2018 | 61-1 v Shrewsbury TownPortsmouth 1-1 Shrewsbury Town | Sky Bet League One |
| 7 | Sat 15 Sep 2018 | 6 2-1 v Peterborough UnitedPeterborough United 1-2 Portsmouth | Sky Bet League One |
| 8 | Sat 22 Sep 2018 | 6 2-2 v Wycombe WanderersPortsmouth 2-2 Wycombe Wanderers | Sky Bet League One |
| 9 | Tue 9 Oct 2018 | 61-0 v Crawley TownCrawley Town 0-1 Portsmouth | Checkatrade Trophy Southern Group A |
| 10 | Sat 27 Oct 2018 | 61-1 v Accrington StanleyAccrington Stanley 1-1 Portsmouth | Sky Bet League One |
| 11 | Sat 10 Nov 2018 | 64-0 v Maidenhead UnitedMaidenhead United 0-4 Portsmouth | Emirates FA Cup First Round |
| 12 | Sat 24 Nov 2018 | 62-1 v Scunthorpe UnitedScunthorpe United 1-2 Portsmouth | Sky Bet League One |
| 13 | Tue 1 Jan 2019 | 62-1 v AFC WimbledonPortsmouth 2-1 AFC Wimbledon | Sky Bet League One |
| 14 | Tue 22 Jan 2019 | 61-0 v Peterborough UnitedPortsmouth 1-0 Peterborough United | Checkatrade Trophy Fourth Round |
| 15 | Sat 2 Feb 2019 | 6 1-1 v Doncaster RoversPortsmouth 1-1 Doncaster Rovers | Sky Bet League One |
| 16 | Tue 5 Feb 2019 | 6 0-2 v Queens Park RangersQueens Park Rangers 2-0 Portsmouth | Emirates FA Cup Fourth Round |
| 17 | Sat 9 Feb 2019 | 61-1 v Plymouth ArgylePlymouth Argyle 1-1 Portsmouth | Sky Bet League One |
| 18 | Sat 16 Feb 2019 | 63-3 v Southend UnitedSouthend United 3-3 Portsmouth | Sky Bet League One |
| 19 | Tue 19 Feb 2019 | 61-1 v Bristol RoversPortsmouth 1-1 Bristol Rovers | Sky Bet League One |
| 20 | Sat 23 Feb 2019 | 60-0 v BarnsleyPortsmouth 0-0 Barnsley | Sky Bet League One |
| 21 | Tue 26 Feb 2019 | 63-0 v BuryBury 0-3 Portsmouth | Checkatrade Trophy Semi Final |
| 22 | Sat 2 Mar 2019 | 65-1 v Bradford CityPortsmouth 5-1 Bradford City | Sky Bet League One |
| 23 | Sat 9 Mar 2019 | 6 1-2 v Charlton AthleticCharlton Athletic 2-1 Portsmouth | Sky Bet League One |
| 24 | Tue 12 Mar 2019 | 63-2 v WalsallWalsall 2-3 Portsmouth | Sky Bet League One |
| 25 | Sat 16 Mar 2019 | 62-0 v Scunthorpe UnitedPortsmouth 2-0 Scunthorpe United | Sky Bet League One |
| 26 | Sat 23 Mar 2019 | 6 2-0 v Shrewsbury TownShrewsbury Town 0-2 Portsmouth | Sky Bet League One |
| 27 | Sun 31 Mar 2019 | 62-2 v SunderlandPortsmouth 2-2 Sunderland | Checkatrade Trophy Final |
| 28 | Sat 6 Apr 2019 | 63-2 v Wycombe WanderersWycombe Wanderers 2-3 Portsmouth | Sky Bet League One |
| 29 | Sat 13 Apr 2019 | 64-1 v RochdalePortsmouth 4-1 Rochdale | Sky Bet League One |
| 30 | Fri 19 Apr 2019 | 62-1 v Burton AlbionBurton Albion 1-2 Portsmouth | Sky Bet League One |
| 31 | Mon 22 Apr 2019 | 62-1 v Coventry CityPortsmouth 2-1 Coventry City | Sky Bet League One |
| 32 | Sat 27 Apr 2019 | 61-1 v SunderlandSunderland 1-1 Portsmouth | Sky Bet League One |
| 33 | Tue 30 Apr 2019 | 62-3 v Peterborough UnitedPortsmouth 2-3 Peterborough United | Sky Bet League One |
| 34 | Sat 4 May 2019 | 61-1 v Accrington StanleyPortsmouth 1-1 Accrington Stanley | Sky Bet League One |
| 35 | Sat 11 May 2019 | 60-1 v SunderlandSunderland 1-0 Portsmouth | Sky Bet League One Play-off Semi Final |
| 36 | Thu 16 May 2019 | 60-0 v SunderlandPortsmouth 0-0 Sunderland | Sky Bet League One Play-off Semi Final |
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