| 1999-12-28 | TorquayvSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | PlymouthvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-12-14 | CarlislevTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | TorquayvShrewsburyLeague Two · England | 3–1 | League Two · England |
| 1999-11-27 | ExetervTorquayLeague Two · England | 3–2 | League Two · England |
| 1999-11-23 | TorquayvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | DarlingtonvTorquayLeague Two · England | 1–1 | League Two · England |
| 1999-11-06 | TorquayvRochdaleLeague Two · England | 1–0 | League Two · England |
| 1999-11-02 | RotherhamvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-10-23 | BarnetvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-10-19 | TorquayvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-10-16 | TorquayvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1999-10-09 | NorthamptonvTorquayLeague Two · England | 3–0 | League Two · England |
| 1999-10-02 | MacclesfieldvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-09-25 | TorquayvBarnetLeague Two · England | 0–1 | League Two · England |
| 1999-09-18 | Leyton OrientvTorquayLeague Two · England | 0–2 | League Two · England |
| 1999-09-11 | TorquayvHullLeague Two · England | 0–1 | League Two · England |
| 1999-09-04 | TorquayvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-08-31 | HalifaxvTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-08-28 | TorquayvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-08-21 | BrightonvTorquayLeague Two · England | 0–1 | League Two · England |
| 1999-08-14 | TorquayvYorkLeague Two · England | 0–0 | League Two · England |
| 1999-08-07 | ShrewsburyvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-05-08 | TorquayvShrewsburyLeague Two · England | 0–3 | League Two · England |
| 1999-05-01 | HullvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | TorquayvRotherhamLeague Two · England | 2–0 | League Two · England |
| 1999-04-17 | PeterborovTorquayLeague Two · England | 4–0 | League Two · England |
| 1999-04-13 | TorquayvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-04-10 | DarlingtonvTorquayLeague Two · England | 0–2 | League Two · England |
| 1999-04-05 | TorquayvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-04-03 | CarlislevTorquayLeague Two · England | 3–0 | League Two · England |
| 1999-03-27 | TorquayvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1999-03-20 | TorquayvScarboroughLeague Two · England | 0–1 | League Two · England |
| 1999-03-13 | CardiffvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-03-09 | PlymouthvTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-03-06 | TorquayvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-03-02 | Leyton OrientvTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-02-27 | SwanseavTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-02-20 | TorquayvChesterLeague Two · England | 0–3 | League Two · England |
| 1999-02-13 | BrentfordvTorquayLeague Two · England | 3–2 | League Two · England |
| 1999-02-06 | TorquayvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-01-30 | SouthendvTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-01-16 | TorquayvRochdaleLeague Two · England | 2–1 | League Two · England |
| 1999-01-09 | CambridgevTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-01-02 | TorquayvBrightonLeague Two · England | 1–1 | League Two · England |