| 1999-12-28 | SwanseavPlymouthLeague Two · England | 1–0 | League Two · England |
| 1999-12-28 | ChestervLeyton OrientLeague Two · England | 1–5 | League Two · England |
| 1999-12-28 | ExetervPeterboroLeague Two · England | 2–2 | League Two · England |
| 1999-12-28 | RochdalevShrewsburyLeague Two · England | 2–1 | League Two · England |
| 1999-12-28 | TorquayvSouthendLeague Two · England | 0–1 | League Two · England |
| 1999-12-28 | NorthamptonvDarlingtonLeague Two · England | 0–3 | League Two · England |
| 1999-12-28 | RotherhamvBrightonLeague Two · England | 1–3 | League Two · England |
| 1999-12-28 | LincolnvHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-28 | YorkvCheltenhamLeague Two · England | 1–2 | League Two · England |
| 1999-12-28 | MacclesfieldvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-28 | HullvMansfieldLeague Two · England | 2–0 | League Two · England |
| 1999-12-28 | BarnetvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | MansfieldvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | HartlepoolvYorkLeague Two · England | 2–1 | League Two · England |
| 1999-12-26 | ShrewsburyvMacclesfieldLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | BrightonvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-12-26 | HalifaxvLincolnLeague Two · England | 3–0 | League Two · England |
| 1999-12-26 | PeterborovRotherhamLeague Two · England | 0–5 | League Two · England |
| 1999-12-26 | DarlingtonvHullLeague Two · England | 0–0 | League Two · England |
| 1999-12-26 | CheltenhamvExeterLeague Two · England | 3–1 | League Two · England |
| 1999-12-26 | Leyton OrientvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-26 | SouthendvNorthamptonLeague Two · England | 2–2 | League Two · England |
| 1999-12-26 | CarlislevRochdaleLeague Two · England | 1–2 | League Two · England |
| 1999-12-26 | PlymouthvTorquayLeague Two · England | 2–2 | League Two · England |
| 1999-12-18 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-12-18 | ExetervHartlepoolLeague Two · England | 1–2 | League Two · England |
| 1999-12-18 | RotherhamvDarlingtonLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | ChestervHalifaxLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | LincolnvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-12-18 | HullvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1999-12-18 | SwanseavBrightonLeague Two · England | 2–0 | League Two · England |
| 1999-12-18 | BarnetvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-12-17 | NorthamptonvPlymouthLeague Two · England | 1–1 | League Two · England |
| 1999-12-17 | YorkvSouthendLeague Two · England | 2–2 | League Two · England |
| 1999-12-15 | DarlingtonvChesterLeague Two · England | 3–1 | League Two · England |
| 1999-12-14 | CarlislevTorquayLeague Two · England | 0–0 | League Two · England |
| 1999-12-11 | HalifaxvRotherhamLeague Two · England | 0–0 | League Two · England |
| 1999-12-11 | CheltenhamvMacclesfieldLeague Two · England | 1–1 | League Two · England |
| 1999-12-11 | HartlepoolvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-11 | ShrewsburyvNorthamptonLeague Two · England | 1–0 | League Two · England |
| 1999-12-10 | BrightonvRochdaleLeague Two · England | 3–4 | League Two · England |
| 1999-12-10 | SouthendvBarnetLeague Two · England | 1–3 | League Two · England |
| 1999-12-04 | HartlepoolvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | BarnetvChesterLeague Two · England | 2–0 | League Two · England |
| 1999-12-04 | DarlingtonvHalifaxLeague Two · England | 4–0 | League Two · England |
| 1999-12-04 | RochdalevCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-12-04 | SwanseavYorkLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | PlymouthvSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | TorquayvShrewsburyLeague Two · England | 3–1 | League Two · England |
| 1999-12-04 | HullvExeterLeague Two · England | 4–0 | League Two · England |