| 2000-03-04 | RotherhamvPlymouthLeague Two · England | 1–1 | League Two · England |
| 2000-02-26 | PlymouthvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 2000-02-22 | LincolnvPlymouthLeague Two · England | 3–0 | League Two · England |
| 2000-02-19 | PlymouthvYorkLeague Two · England | 2–0 | League Two · England |
| 2000-02-12 | BrightonvPlymouthLeague Two · England | 1–1 | League Two · England |
| 2000-02-05 | PlymouthvCarlisleLeague Two · England | 2–0 | League Two · England |
| 2000-01-29 | PeterborovPlymouthLeague Two · England | 2–0 | League Two · England |
| 2000-01-22 | PlymouthvHalifaxLeague Two · England | 1–1 | League Two · England |
| 2000-01-15 | ShrewsburyvPlymouthLeague Two · England | 0–0 | League Two · England |
| 2000-01-03 | PlymouthvMacclesfieldLeague Two · England | 3–2 | League Two · England |
| 1999-12-28 | SwanseavPlymouthLeague Two · England | 1–0 | League Two · England |
| 1999-12-26 | PlymouthvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-12-17 | NorthamptonvPlymouthLeague Two · England | 1–1 | League Two · England |
| 1999-12-04 | PlymouthvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-11-27 | YorkvPlymouthLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | CheltenhamvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-11-14 | PlymouthvBarnetLeague Two · England | 4–1 | League Two · England |
| 1999-11-06 | ChestervPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-11-02 | PlymouthvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-10-23 | PlymouthvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-10-19 | HullvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-10-16 | RochdalevPlymouthLeague Two · England | 0–0 | League Two · England |
| 1999-10-09 | PlymouthvMansfieldLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | PlymouthvLeyton OrientLeague Two · England | 5–0 | League Two · England |
| 1999-09-25 | DarlingtonvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-09-18 | HartlepoolvPlymouthLeague Two · England | 3–0 | League Two · England |
| 1999-09-11 | PlymouthvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-09-05 | PlymouthvBrightonLeague Two · England | 3–3 | League Two · England |
| 1999-08-30 | CarlislevPlymouthLeague Two · England | 4–2 | League Two · England |
| 1999-08-28 | PlymouthvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-08-21 | HalifaxvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-08-14 | PlymouthvShrewsburyLeague Two · England | 0–0 | League Two · England |
| 1999-08-07 | SouthendvPlymouthLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | CarlislevPlymouthLeague Two · England | 2–1 | League Two · England |
| 1999-05-05 | ScarboroughvPlymouthLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | PlymouthvCambridgeLeague Two · England | 2–2 | League Two · England |
| 1999-04-24 | SwanseavPlymouthLeague Two · England | 2–3 | League Two · England |
| 1999-04-17 | PlymouthvSouthendLeague Two · England | 0–3 | League Two · England |
| 1999-04-13 | Leyton OrientvPlymouthLeague Two · England | 4–3 | League Two · England |
| 1999-04-10 | PlymouthvBrightonLeague Two · England | 1–2 | League Two · England |
| 1999-04-05 | BrentfordvPlymouthLeague Two · England | 3–1 | League Two · England |
| 1999-04-03 | PlymouthvShrewsburyLeague Two · England | 2–0 | League Two · England |
| 1999-03-30 | PlymouthvScunthorpeLeague Two · England | 5–0 | League Two · England |
| 1999-03-27 | ChestervPlymouthLeague Two · England | 3–2 | League Two · England |
| 1999-03-20 | HullvPlymouthLeague Two · England | 1–0 | League Two · England |
| 1999-03-13 | PlymouthvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-03-09 | PlymouthvTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | PlymouthvPeterboroLeague Two · England | 0–2 | League Two · England |
| 1999-02-23 | PlymouthvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-02-20 | DarlingtonvPlymouthLeague Two · England | 1–2 | League Two · England |