| 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 |
| 1999-12-04 | NorthamptonvMacclesfieldLeague Two · England | 2–0 | League Two · England |
| 1999-12-04 | RotherhamvLincolnLeague Two · England | 1–1 | League Two · England |
| 1999-12-04 | Leyton OrientvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | ChestervSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | PeterborovBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-11-27 | CarlislevRotherhamLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | ExetervTorquayLeague Two · England | 3–2 | League Two · England |
| 1999-11-27 | SouthendvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 1999-11-27 | ShrewsburyvHullLeague Two · England | 3–0 | League Two · England |
| 1999-11-27 | HalifaxvMansfieldLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | CheltenhamvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1999-11-27 | MacclesfieldvHartlepoolLeague Two · England | 3–3 | League Two · England |
| 1999-11-27 | YorkvPlymouthLeague Two · England | 0–0 | League Two · England |
| 1999-11-27 | LincolnvRochdaleLeague Two · England | 1–1 | League Two · England |
| 1999-11-27 | BrightonvNorthamptonLeague Two · England | 1–3 | League Two · England |
| 1999-11-23 | TorquayvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | MansfieldvRotherhamLeague Two · England | 1–2 | League Two · England |
| 1999-11-23 | HullvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-11-23 | ChestervSouthendLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | YorkvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-11-23 | Leyton OrientvRochdaleLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | ExetervNorthamptonLeague Two · England | 1–2 | League Two · England |
| 1999-11-23 | BrightonvLincolnLeague Two · England | 2–2 | League Two · England |
| 1999-11-23 | SwanseavDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-11-23 | CheltenhamvPlymouthLeague Two · England | 2–0 | League Two · England |
| 1999-11-23 | BarnetvCarlisleLeague Two · England | 3–0 | League Two · England |
| 1999-11-20 | PeterborovMacclesfieldLeague Two · England | 2–2 | League Two · England |
| 1999-11-16 | SwanseavCheltenhamLeague Two · England | 0–0 | League Two · England |
| 1999-11-14 | PlymouthvBarnetLeague Two · England | 4–1 | League Two · England |
| 1999-11-14 | MacclesfieldvBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-11-14 | RochdalevMansfieldLeague Two · England | 2–1 | League Two · England |
| 1999-11-13 | HartlepoolvChesterLeague Two · England | 1–0 | League Two · England |
| 1999-11-12 | HalifaxvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-11-12 | DarlingtonvTorquayLeague Two · England | 1–1 | League Two · England |
| 1999-11-12 | LincolnvYorkLeague Two · England | 4–2 | League Two · England |
| 1999-11-12 | NorthamptonvCheltenhamLeague Two · England | 3–2 | League Two · England |
| 1999-11-12 | RotherhamvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 1999-11-12 | ShrewsburyvSwanseaLeague Two · England | 1–1 | League Two · England |
| 1999-11-12 | CarlislevPeterboroLeague Two · England | 1–1 | League Two · England |