| 2018-12-29 | Fleetwood TownvPortsmouthLeague One · England | 2–5 | League One · England |
| 2018-12-26 | GillinghamvPortsmouthLeague One · England | 2–0 | League One · England |
| 2018-12-22 | PortsmouthvSunderlandLeague One · England | 3–1 | League One · England |
| 2018-12-15 | BarnsleyvPortsmouthLeague One · England | 1–1 | League One · England |
| 2018-12-11 | PortsmouthvCharltonLeague One · England | 1–2 | League One · England |
| 2018-12-08 | PortsmouthvSouthendLeague One · England | 2–0 | League One · England |
| 2018-11-27 | PortsmouthvWalsallLeague One · England | 2–0 | League One · England |
| 2018-11-24 | ScunthorpevPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-11-03 | BradfordvPortsmouthLeague One · England | 0–1 | League One · England |
| 2018-10-27 | AccringtonvPortsmouthLeague One · England | 1–1 | League One · England |
| 2018-10-23 | PortsmouthvBurtonLeague One · England | 2–2 | League One · England |
| 2018-10-20 | PortsmouthvFleetwood TownLeague One · England | 1–0 | League One · England |
| 2018-10-13 | AFC WimbledonvPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-10-06 | PortsmouthvGillinghamLeague One · England | 0–2 | League One · England |
| 2018-10-02 | CoventryvPortsmouthLeague One · England | 0–1 | League One · England |
| 2018-09-29 | RochdalevPortsmouthLeague One · England | 1–3 | League One · England |
| 2018-09-22 | PortsmouthvWycombeLeague One · England | 2–2 | League One · England |
| 2018-09-15 | PeterborovPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-09-08 | PortsmouthvShrewsburyLeague One · England | 1–1 | League One · England |
| 2018-09-01 | PortsmouthvPlymouthLeague One · England | 3–0 | League One · England |
| 2018-08-25 | DoncastervPortsmouthLeague One · England | 0–0 | League One · England |
| 2018-08-21 | Bristol RvsvPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-08-18 | PortsmouthvOxfordLeague One · England | 4–1 | League One · England |
| 2018-08-11 | BlackpoolvPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-08-04 | PortsmouthvLutonLeague One · England | 1–0 | League One · England |
| 2018-05-05 | PortsmouthvPeterboroLeague One · England | 2–0 | League One · England |
| 2018-04-28 | BuryvPortsmouthLeague One · England | 1–0 | League One · England |
| 2018-04-21 | PortsmouthvCharltonLeague One · England | 0–1 | League One · England |
| 2018-04-17 | BradfordvPortsmouthLeague One · England | 3–1 | League One · England |
| 2018-04-14 | PlymouthvPortsmouthLeague One · England | 0–0 | League One · England |
| 2018-04-07 | RochdalevPortsmouthLeague One · England | 3–3 | League One · England |
| 2018-04-02 | PortsmouthvWiganLeague One · England | 2–1 | League One · England |
| 2018-03-31 | WalsallvPortsmouthLeague One · England | 0–1 | League One · England |
| 2018-03-25 | PortsmouthvOxfordLeague One · England | 3–0 | League One · England |
| 2018-03-17 | OldhamvPortsmouthLeague One · England | 0–2 | League One · England |
| 2018-03-10 | PortsmouthvGillinghamLeague One · England | 1–3 | League One · England |
| 2018-02-24 | PortsmouthvBlackpoolLeague One · England | 0–2 | League One · England |
| 2018-02-20 | Fleetwood TownvPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-02-17 | SouthendvPortsmouthLeague One · England | 3–1 | League One · England |
| 2018-02-13 | PortsmouthvBlackburnLeague One · England | 1–2 | League One · England |
| 2018-02-10 | Milton Keynes DonsvPortsmouthLeague One · England | 1–2 | League One · England |
| 2018-02-03 | PortsmouthvDoncasterLeague One · England | 2–2 | League One · England |
| 2018-01-27 | PortsmouthvShrewsburyLeague One · England | 0–1 | League One · England |
| 2018-01-20 | RotherhamvPortsmouthLeague One · England | 1–0 | League One · England |
| 2018-01-13 | PortsmouthvScunthorpeLeague One · England | 1–1 | League One · England |
| 2018-01-01 | Bristol RvsvPortsmouthLeague One · England | 2–1 | League One · England |