| 1999-11-12 | SouthendvHullLeague Two · England | 1–2 | League Two · England |
| 1999-11-06 | CheltenhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-11-06 | ChestervPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-11-06 | Leyton OrientvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 1999-11-06 | TorquayvRochdaleLeague Two · England | 1–0 | League Two · England |
| 1999-11-06 | YorkvMacclesfieldLeague Two · England | 0–2 | League Two · England |
| 1999-11-06 | BrightonvHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1999-11-06 | HullvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-06 | MansfieldvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-11-06 | PeterborovShrewsburyLeague Two · England | 4–1 | League Two · England |
| 1999-11-06 | ExetervSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-11-06 | BarnetvDarlingtonLeague Two · England | 1–0 | League Two · England |
| 1999-11-05 | SwanseavHalifaxLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | LincolnvPeterboroLeague Two · England | 1–2 | League Two · England |
| 1999-11-02 | CarlislevYorkLeague Two · England | 0–1 | League Two · England |
| 1999-11-02 | MacclesfieldvMansfieldLeague Two · England | 5–2 | League Two · England |
| 1999-11-02 | ShrewsburyvChesterLeague Two · England | 0–1 | League Two · England |
| 1999-11-02 | DarlingtonvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-11-02 | RochdalevHullLeague Two · England | 0–2 | League Two · England |
| 1999-11-02 | HalifaxvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 1999-11-02 | SouthendvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-11-02 | RotherhamvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-11-02 | PlymouthvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-11-02 | NorthamptonvSwanseaLeague Two · England | 2–1 | League Two · England |
| 1999-11-02 | HartlepoolvBarnetLeague Two · England | 3–0 | League Two · England |
| 1999-10-23 | PlymouthvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-10-23 | BarnetvTorquayLeague Two · England | 1–2 | League Two · England |
| 1999-10-23 | NorthamptonvRotherhamLeague Two · England | 0–1 | League Two · England |
| 1999-10-23 | MacclesfieldvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-10-23 | CarlislevHalifaxLeague Two · England | 1–1 | League Two · England |
| 1999-10-23 | LincolnvChesterLeague Two · England | 4–1 | League Two · England |
| 1999-10-23 | YorkvHullLeague Two · England | 1–1 | League Two · England |
| 1999-10-23 | CheltenhamvBrightonLeague Two · England | 0–0 | League Two · England |
| 1999-10-23 | ShrewsburyvMansfieldLeague Two · England | 1–2 | League Two · England |
| 1999-10-23 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-10-23 | PeterborovSouthendLeague Two · England | 1–0 | League Two · England |
| 1999-10-22 | SwanseavRochdaleLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | ExetervSwanseaLeague Two · England | 1–1 | League Two · England |
| 1999-10-19 | ChestervCheltenhamLeague Two · England | 2–1 | League Two · England |
| 1999-10-19 | DarlingtonvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-10-19 | Leyton OrientvBarnetLeague Two · England | 0–0 | League Two · England |
| 1999-10-19 | HullvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-10-19 | SouthendvLincolnLeague Two · England | 2–2 | League Two · England |
| 1999-10-19 | RotherhamvHartlepoolLeague Two · England | 3–0 | League Two · England |
| 1999-10-19 | BrightonvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | TorquayvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-10-19 | RochdalevMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-10-19 | HalifaxvYorkLeague Two · England | 0–2 | League Two · England |
| 1999-10-19 | MansfieldvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 1999-10-16 | DarlingtonvCheltenhamLeague Two · England | 1–0 | League Two · England |