| 2019-12-29 | Milton Keynes DonsvPortsmouthLeague One · England | 3–1 | League One · England |
| 2019-12-26 | PortsmouthvWycombeLeague One · England | 2–0 | League One · England |
| 2019-12-21 | PortsmouthvIpswichLeague One · England | 1–0 | League One · England |
| 2019-12-14 | AccringtonvPortsmouthLeague One · England | 4–1 | League One · England |
| 2019-12-07 | PortsmouthvPeterboroLeague One · England | 2–2 | League One · England |
| 2019-11-26 | PortsmouthvRotherhamLeague One · England | 3–2 | League One · England |
| 2019-11-23 | RochdalevPortsmouthLeague One · England | 0–3 | League One · England |
| 2019-11-05 | PortsmouthvSouthendLeague One · England | 4–1 | League One · England |
| 2019-11-02 | PortsmouthvOxfordLeague One · England | 1–1 | League One · England |
| 2019-10-26 | Bristol RvsvPortsmouthLeague One · England | 2–2 | League One · England |
| 2019-10-22 | PortsmouthvLincolnLeague One · England | 1–0 | League One · England |
| 2019-10-19 | AFC WimbledonvPortsmouthLeague One · England | 1–0 | League One · England |
| 2019-10-12 | PortsmouthvGillinghamLeague One · England | 0–0 | League One · England |
| 2019-10-05 | DoncastervPortsmouthLeague One · England | 1–2 | League One · England |
| 2019-09-28 | PortsmouthvBoltonLeague One · England | 1–0 | League One · England |
| 2019-09-21 | WycombevPortsmouthLeague One · England | 1–0 | League One · England |
| 2019-09-17 | PortsmouthvBurtonLeague One · England | 2–2 | League One · England |
| 2019-08-31 | BlackpoolvPortsmouthLeague One · England | 1–1 | League One · England |
| 2019-08-20 | PortsmouthvCoventryLeague One · England | 3–3 | League One · England |
| 2019-08-17 | SunderlandvPortsmouthLeague One · England | 2–1 | League One · England |
| 2019-08-10 | PortsmouthvTranmereLeague One · England | 2–0 | League One · England |
| 2019-08-03 | ShrewsburyvPortsmouthLeague One · England | 1–0 | League One · England |
| 2019-05-04 | PortsmouthvAccringtonLeague One · England | 1–1 | League One · England |
| 2019-04-30 | PortsmouthvPeterboroLeague One · England | 2–3 | League One · England |
| 2019-04-27 | SunderlandvPortsmouthLeague One · England | 1–1 | League One · England |
| 2019-04-22 | PortsmouthvCoventryLeague One · England | 2–1 | League One · England |
| 2019-04-19 | BurtonvPortsmouthLeague One · England | 1–2 | League One · England |
| 2019-04-13 | PortsmouthvRochdaleLeague One · England | 4–1 | League One · England |
| 2019-04-06 | WycombevPortsmouthLeague One · England | 2–3 | League One · England |
| 2019-03-23 | ShrewsburyvPortsmouthLeague One · England | 0–2 | League One · England |
| 2019-03-16 | PortsmouthvScunthorpeLeague One · England | 2–0 | League One · England |
| 2019-03-12 | WalsallvPortsmouthLeague One · England | 2–3 | League One · England |
| 2019-03-09 | CharltonvPortsmouthLeague One · England | 2–1 | League One · England |
| 2019-03-02 | PortsmouthvBradfordLeague One · England | 5–1 | League One · England |
| 2019-02-23 | PortsmouthvBarnsleyLeague One · England | 0–0 | League One · England |
| 2019-02-19 | PortsmouthvBristol RvsLeague One · England | 1–1 | League One · England |
| 2019-02-16 | SouthendvPortsmouthLeague One · England | 3–3 | League One · England |
| 2019-02-09 | PlymouthvPortsmouthLeague One · England | 1–1 | League One · England |
| 2019-02-02 | PortsmouthvDoncasterLeague One · England | 1–1 | League One · England |
| 2019-01-29 | LutonvPortsmouthLeague One · England | 3–2 | League One · England |
| 2019-01-19 | OxfordvPortsmouthLeague One · England | 2–1 | League One · England |
| 2019-01-12 | PortsmouthvBlackpoolLeague One · England | 0–1 | League One · England |
| 2019-01-01 | PortsmouthvAFC WimbledonLeague One · England | 2–1 | League One · England |