| 1999-02-27 | SwanseavTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | BrightonvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-02-27 | BrentfordvScarboroughLeague Two · England | 1–1 | League Two · England |
| 1999-02-27 | ShrewsburyvDarlingtonLeague Two · England | 3–0 | League Two · England |
| 1999-02-27 | ChestervCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-02-27 | HalifaxvHullLeague Two · England | 0–1 | League Two · England |
| 1999-02-27 | HartlepoolvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-02-27 | CambridgevSouthendLeague Two · England | 3–0 | League Two · England |
| 1999-02-27 | BarnetvExeterLeague Two · England | 0–1 | League Two · England |
| 1999-02-23 | SwanseavMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-02-23 | PlymouthvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-02-20 | HullvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-02-20 | CarlislevMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-02-20 | RotherhamvBrentfordLeague Two · England | 2–4 | League Two · England |
| 1999-02-20 | TorquayvChesterLeague Two · England | 0–3 | League Two · England |
| 1999-02-20 | SouthendvBrightonLeague Two · England | 3–0 | League Two · England |
| 1999-02-20 | ExetervHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-02-20 | Leyton OrientvCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-02-20 | DarlingtonvPlymouthLeague Two · England | 1–2 | League Two · England |
| 1999-02-20 | PeterborovShrewsburyLeague Two · England | 2–2 | League Two · England |
| 1999-02-20 | ScunthorpevRochdaleLeague Two · England | 0–1 | League Two · England |
| 1999-02-20 | ScarboroughvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-02-19 | CardiffvHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-02-16 | SwanseavBrentfordLeague Two · England | 2–1 | League Two · England |
| 1999-02-16 | DarlingtonvHullLeague Two · England | 0–1 | League Two · England |
| 1999-02-13 | BrentfordvTorquayLeague Two · England | 3–2 | League Two · England |
| 1999-02-13 | HartlepoolvDarlingtonLeague Two · England | 2–3 | League Two · England |
| 1999-02-13 | MansfieldvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-02-13 | BarnetvCardiffLeague Two · England | 1–0 | League Two · England |
| 1999-02-13 | SwanseavCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-02-13 | HalifaxvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-02-13 | CambridgevScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1999-02-13 | PlymouthvRotherhamLeague Two · England | 1–0 | League Two · England |
| 1999-02-13 | BrightonvExeterLeague Two · England | 0–1 | League Two · England |
| 1999-02-13 | ShrewsburyvScarboroughLeague Two · England | 3–1 | League Two · England |
| 1999-02-13 | ChestervPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-02-12 | RochdalevHullLeague Two · England | 3–0 | League Two · England |
| 1999-02-06 | BrentfordvHullLeague Two · England | 0–2 | League Two · England |
| 1999-02-06 | ChestervExeterLeague Two · England | 0–0 | League Two · England |
| 1999-02-06 | PeterborovBarnetLeague Two · England | 5–2 | League Two · England |
| 1999-02-06 | RotherhamvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-02-06 | ShrewsburyvRochdaleLeague Two · England | 3–2 | League Two · England |
| 1999-02-06 | DarlingtonvMansfieldLeague Two · England | 5–1 | League Two · England |
| 1999-02-06 | PlymouthvCardiffLeague Two · England | 1–1 | League Two · England |
| 1999-02-06 | ScarboroughvCambridgeLeague Two · England | 1–5 | League Two · England |
| 1999-02-06 | CarlislevLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-02-06 | HartlepoolvHalifaxLeague Two · England | 2–0 | League Two · England |
| 1999-02-06 | TorquayvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-02-05 | SwanseavBrightonLeague Two · England | 2–2 | League Two · England |
| 1999-02-02 | BrentfordvCarlisleLeague Two · England | 1–1 | League Two · England |