| 1999-05-01 | HartlepoolvCarlisleLeague Two · England | 0–0 | League Two · England |
| 1999-05-01 | PeterborovLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | BarnetvSouthendLeague Two · England | 0–2 | League Two · England |
| 1999-05-01 | HalifaxvScarboroughLeague Two · England | 1–2 | League Two · England |
| 1999-05-01 | HullvTorquayLeague Two · England | 1–0 | League Two · England |
| 1999-05-01 | BrentfordvExeterLeague Two · England | 3–0 | League Two · England |
| 1999-05-01 | PlymouthvCambridgeLeague Two · England | 2–2 | League Two · England |
| 1999-05-01 | RochdalevSwanseaLeague Two · England | 0–3 | League Two · England |
| 1999-05-01 | ShrewsburyvMansfieldLeague Two · England | 1–0 | League Two · England |
| 1999-04-27 | RotherhamvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-04-27 | DarlingtonvBrentfordLeague Two · England | 2–2 | League Two · England |
| 1999-04-27 | HalifaxvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1999-04-27 | RochdalevCambridgeLeague Two · England | 0–2 | League Two · England |
| 1999-04-27 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-04-27 | MansfieldvExeterLeague Two · England | 0–1 | League Two · England |
| 1999-04-24 | ExetervRochdaleLeague Two · England | 2–1 | League Two · England |
| 1999-04-24 | ScarboroughvCardiffLeague Two · England | 1–2 | League Two · England |
| 1999-04-24 | MansfieldvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1999-04-24 | ChestervHalifaxLeague Two · England | 2–2 | League Two · England |
| 1999-04-24 | SouthendvBrentfordLeague Two · England | 1–4 | League Two · England |
| 1999-04-24 | Leyton OrientvShrewsburyLeague Two · England | 6–1 | League Two · England |
| 1999-04-24 | CambridgevPeterboroLeague Two · England | 1–1 | League Two · England |
| 1999-04-24 | ScunthorpevBarnetLeague Two · England | 3–1 | League Two · England |
| 1999-04-24 | BrightonvHullLeague Two · England | 0–0 | League Two · England |
| 1999-04-24 | SwanseavPlymouthLeague Two · England | 2–3 | League Two · England |
| 1999-04-24 | CarlislevDarlingtonLeague Two · England | 3–3 | League Two · England |
| 1999-04-24 | TorquayvRotherhamLeague Two · England | 2–0 | League Two · England |
| 1999-04-21 | ScarboroughvLeyton OrientLeague Two · England | 1–3 | League Two · England |
| 1999-04-20 | ShrewsburyvRotherhamLeague Two · England | 2–3 | League Two · England |
| 1999-04-18 | CardiffvSwanseaLeague Two · England | 0–0 | League Two · England |
| 1999-04-17 | RotherhamvCarlisleLeague Two · England | 3–1 | League Two · England |
| 1999-04-17 | HartlepoolvScarboroughLeague Two · England | 3–0 | League Two · England |
| 1999-04-17 | ShrewsburyvExeterLeague Two · England | 1–1 | League Two · England |
| 1999-04-17 | DarlingtonvCambridgeLeague Two · England | 0–0 | League Two · England |
| 1999-04-17 | RochdalevChesterLeague Two · England | 3–1 | League Two · England |
| 1999-04-17 | PlymouthvSouthendLeague Two · England | 0–3 | League Two · England |
| 1999-04-17 | BrentfordvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1999-04-17 | HullvScunthorpeLeague Two · England | 2–3 | League Two · England |
| 1999-04-17 | BarnetvMansfieldLeague Two · England | 0–0 | League Two · England |
| 1999-04-17 | PeterborovTorquayLeague Two · England | 4–0 | League Two · England |
| 1999-04-17 | HalifaxvBrightonLeague Two · England | 1–0 | League Two · England |
| 1999-04-14 | ScarboroughvDarlingtonLeague Two · England | 0–2 | League Two · England |
| 1999-04-13 | Leyton OrientvPlymouthLeague Two · England | 4–3 | League Two · England |
| 1999-04-13 | BrightonvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 1999-04-13 | ExetervRotherhamLeague Two · England | 3–0 | League Two · England |
| 1999-04-13 | TorquayvBarnetLeague Two · England | 1–1 | League Two · England |
| 1999-04-13 | MansfieldvHalifaxLeague Two · England | 0–1 | League Two · England |
| 1999-04-13 | SwanseavHartlepoolLeague Two · England | 1–0 | League Two · England |
| 1999-04-13 | CarlislevHullLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | CambridgevRochdaleLeague Two · England | 1–1 | League Two · England |