| 1 | Sat 2 Feb 2019 | 1-1 v Doncaster RoversPortsmouth 1-1 Doncaster Rovers | Sky Bet League One |
| 2 | Sat 9 Feb 2019 | 1-1 v Plymouth ArgylePlymouth Argyle 1-1 Portsmouth | Sky Bet League One |
| 3 | Sat 16 Feb 2019 | 3-3 v Southend UnitedSouthend United 3-3 Portsmouth | Sky Bet League One |
| 4 | Tue 19 Feb 2019 | 1-1 v Bristol RoversPortsmouth 1-1 Bristol Rovers | Sky Bet League One |
| 5 | Sat 23 Feb 2019 | 0-0 v BarnsleyPortsmouth 0-0 Barnsley | Sky Bet League One |
| 6 | Tue 12 Mar 2019 | 3-2 v WalsallWalsall 2-3 Portsmouth | Sky Bet League One |
| 7 | Sat 16 Mar 2019 | 2-0 v Scunthorpe UnitedPortsmouth 2-0 Scunthorpe United | Sky Bet League One |
| 8 | Sat 23 Mar 2019 | 2-0 v Shrewsbury TownShrewsbury Town 0-2 Portsmouth | Sky Bet League One |
| 9 | Sun 31 Mar 2019 | 2-2 v SunderlandPortsmouth 2-2 Sunderland | Checkatrade Trophy Final |
| 10 | Sat 13 Apr 2019 | 4-1 v RochdalePortsmouth 4-1 Rochdale | Sky Bet League One |
| 11 | Fri 19 Apr 2019 | 2-1 v Burton AlbionBurton Albion 1-2 Portsmouth | Sky Bet League One |
| 12 | Tue 30 Apr 2019 | 2-3 v Peterborough UnitedPortsmouth 2-3 Peterborough United | Sky Bet League One |
| 13 | Sat 4 May 2019 | 1-1 v Accrington StanleyPortsmouth 1-1 Accrington Stanley | Sky Bet League One |
| 14 | Sat 11 May 2019 | 0-1 v SunderlandSunderland 1-0 Portsmouth | Sky Bet League One Play-off Semi Final |
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