| 1999-09-11 | MansfieldvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-09-11 | HalifaxvBrightonLeague Two · England | 2–1 | League Two · England |
| 1999-09-11 | PlymouthvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-09-11 | CarlislevLincolnLeague Two · England | 1–0 | League Two · England |
| 1999-09-11 | ChestervExeterLeague Two · England | 1–1 | League Two · England |
| 1999-09-11 | MacclesfieldvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-09-11 | NorthamptonvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-09-11 | RochdalevDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1999-09-11 | YorkvPeterboroLeague Two · England | 0–0 | League Two · England |
| 1999-09-11 | SwanseavBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-09-05 | BarnetvMacclesfieldLeague Two · England | 2–1 | League Two · England |
| 1999-09-05 | PlymouthvBrightonLeague Two · England | 3–3 | League Two · England |
| 1999-09-04 | DarlingtonvExeterLeague Two · England | 1–0 | League Two · England |
| 1999-09-04 | HartlepoolvSouthendLeague Two · England | 1–2 | League Two · England |
| 1999-09-04 | TorquayvLincolnLeague Two · England | 5–2 | League Two · England |
| 1999-09-04 | RotherhamvYorkLeague Two · England | 1–0 | League Two · England |
| 1999-09-04 | NorthamptonvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-09-03 | Leyton OrientvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-09-03 | MansfieldvPeterboroLeague Two · England | 3–1 | League Two · England |
| 1999-09-03 | RochdalevHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-09-03 | HullvChesterLeague Two · England | 2–1 | League Two · England |
| 1999-08-31 | HalifaxvTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-08-31 | ShrewsburyvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 1999-08-31 | BrightonvHullLeague Two · England | 3–0 | League Two · England |
| 1999-08-30 | PeterborovDarlingtonLeague Two · England | 4–2 | League Two · England |
| 1999-08-30 | CheltenhamvBarnetLeague Two · England | 1–2 | League Two · England |
| 1999-08-30 | MacclesfieldvRotherhamLeague Two · England | 1–1 | League Two · England |
| 1999-08-30 | ExetervMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-08-30 | LincolnvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-08-30 | CarlislevPlymouthLeague Two · England | 4–2 | League Two · England |
| 1999-08-30 | ChestervRochdaleLeague Two · England | 0–2 | League Two · England |
| 1999-08-30 | SouthendvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-08-30 | YorkvNorthamptonLeague Two · England | 0–1 | League Two · England |
| 1999-08-28 | TorquayvChesterLeague Two · England | 2–2 | League Two · England |
| 1999-08-28 | RochdalevExeterLeague Two · England | 0–2 | League Two · England |
| 1999-08-28 | Leyton OrientvHalifaxLeague Two · England | 1–0 | League Two · England |
| 1999-08-28 | HartlepoolvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 1999-08-28 | PlymouthvPeterboroLeague Two · England | 2–1 | League Two · England |
| 1999-08-28 | SwanseavSouthendLeague Two · England | 3–1 | League Two · England |
| 1999-08-28 | DarlingtonvBrightonLeague Two · England | 1–1 | League Two · England |
| 1999-08-28 | HullvMacclesfieldLeague Two · England | 2–3 | League Two · England |
| 1999-08-28 | BarnetvYorkLeague Two · England | 6–3 | League Two · England |
| 1999-08-28 | RotherhamvShrewsburyLeague Two · England | 4–0 | League Two · England |
| 1999-08-28 | MansfieldvCarlisleLeague Two · England | 1–1 | League Two · England |
| 1999-08-27 | NorthamptonvLincolnLeague Two · England | 1–0 | League Two · England |
| 1999-08-21 | CarlislevHartlepoolLeague Two · England | 0–3 | League Two · England |
| 1999-08-21 | YorkvRochdaleLeague Two · England | 0–3 | League Two · England |
| 1999-08-21 | HalifaxvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1999-08-21 | BrightonvTorquayLeague Two · England | 0–1 | League Two · England |
| 1999-08-21 | ExetervRotherhamLeague Two · England | 3–1 | League Two · England |