| 1998-12-28 | PlymouthvExeterLeague Two · England | 1–0 | League Two · England |
| 1998-12-26 | BarnetvPlymouthLeague Two · England | 1–1 | League Two · England |
| 1998-12-19 | PlymouthvCarlisleLeague Two · England | 2–0 | League Two · England |
| 1998-12-12 | CambridgevPlymouthLeague Two · England | 1–0 | League Two · England |
| 1998-11-28 | PlymouthvLeyton OrientLeague Two · England | 2–4 | League Two · England |
| 1998-11-21 | SouthendvPlymouthLeague Two · England | 1–0 | League Two · England |
| 1998-11-10 | PlymouthvSwanseaLeague Two · England | 1–2 | League Two · England |
| 1998-11-07 | HartlepoolvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1998-11-03 | PlymouthvBrentfordLeague Two · England | 3–0 | League Two · England |
| 1998-10-31 | PlymouthvHullLeague Two · England | 0–0 | League Two · England |
| 1998-10-20 | BrightonvPlymouthLeague Two · England | 1–3 | League Two · England |
| 1998-10-17 | ShrewsburyvPlymouthLeague Two · England | 2–1 | League Two · England |
| 1998-10-03 | TorquayvPlymouthLeague Two · England | 1–1 | League Two · England |
| 1998-09-27 | PlymouthvScarboroughLeague Two · England | 0–0 | League Two · England |
| 1998-09-19 | PeterborovPlymouthLeague Two · England | 0–2 | League Two · England |
| 1998-09-12 | PlymouthvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1998-09-08 | RotherhamvPlymouthLeague Two · England | 0–2 | League Two · England |
| 1998-09-05 | CardiffvPlymouthLeague Two · England | 1–0 | League Two · England |
| 1998-08-31 | PlymouthvHalifaxLeague Two · England | 1–0 | League Two · England |
| 1998-08-29 | ScunthorpevPlymouthLeague Two · England | 0–2 | League Two · England |
| 1998-08-22 | PlymouthvBarnetLeague Two · England | 2–0 | League Two · England |
| 1998-08-15 | MansfieldvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1998-08-08 | PlymouthvRochdaleLeague Two · England | 2–1 | League Two · England |