| 1999-11-14 | Crystal PalacevQPRChampionship · England | 3–0 | Championship · England |
| 1999-11-14 | Nott'm ForestvHuddersfieldChampionship · England | 1–3 | Championship · England |
| 1999-11-14 | West BromvPortsmouthChampionship · England | 3–2 | Championship · England |
| 1999-11-14 | Sheffield UnitedvBoltonChampionship · England | 1–2 | Championship · England |
| 1999-11-13 | FulhamvBarnsleyChampionship · England | 1–3 | Championship · England |
| 1999-11-12 | GrimsbyvCharltonChampionship · England | 2–5 | Championship · England |
| 1999-11-12 | IpswichvTranmereChampionship · England | 0–0 | Championship · England |
| 1999-11-12 | SwindonvNorwichChampionship · England | 0–0 | Championship · England |
| 1999-11-12 | WalsallvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-11-09 | FulhamvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-11-06 | TranmerevWest BromChampionship · England | 3–0 | Championship · England |
| 1999-11-06 | BarnsleyvSheffield UnitedChampionship · England | 2–0 | Championship · England |
| 1999-11-06 | CharltonvWalsallChampionship · England | 2–1 | Championship · England |
| 1999-11-06 | NorwichvNott'm ForestChampionship · England | 1–0 | Championship · England |
| 1999-11-06 | BlackburnvIpswichChampionship · England | 2–2 | Championship · England |
| 1999-11-06 | WolvesvGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-11-06 | StockportvFulhamChampionship · England | 2–1 | Championship · England |
| 1999-11-06 | QPRvMan CityChampionship · England | 1–1 | Championship · England |
| 1999-11-06 | BoltonvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-11-06 | HuddersfieldvSwindonChampionship · England | 4–0 | Championship · England |
| 1999-11-06 | PortsmouthvBirminghamChampionship · England | 2–2 | Championship · England |
| 1999-11-05 | Port ValevCreweChampionship · England | 1–0 | Championship · England |
| 1999-11-03 | Man CityvPortsmouthChampionship · England | 4–2 | Championship · England |
| 1999-11-02 | CrewevCharltonChampionship · England | 0–2 | Championship · England |
| 1999-11-02 | HuddersfieldvIpswichChampionship · England | 3–1 | Championship · England |
| 1999-11-02 | StockportvQPRChampionship · England | 3–3 | Championship · England |
| 1999-10-31 | West BromvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-10-30 | FulhamvNorwichChampionship · England | 1–1 | Championship · England |
| 1999-10-30 | Sheffield UnitedvHuddersfieldChampionship · England | 0–1 | Championship · England |
| 1999-10-30 | StockportvWalsallChampionship · England | 1–1 | Championship · England |
| 1999-10-30 | PortsmouthvCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-10-30 | BarnsleyvNott'm ForestChampionship · England | 1–0 | Championship · England |
| 1999-10-30 | Port ValevMan CityChampionship · England | 1–2 | Championship · England |
| 1999-10-30 | BoltonvSwindonChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | TranmerevCreweChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | BirminghamvCharltonChampionship · England | 1–0 | Championship · England |
| 1999-10-30 | IpswichvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | BlackburnvQPRChampionship · England | 0–2 | Championship · England |
| 1999-10-27 | Nott'm ForestvBoltonChampionship · England | 1–1 | Championship · England |
| 1999-10-27 | QPRvBirminghamChampionship · England | 2–2 | Championship · England |
| 1999-10-27 | Man CityvIpswichChampionship · England | 1–0 | Championship · England |
| 1999-10-26 | NorwichvStockportChampionship · England | 2–0 | Championship · England |
| 1999-10-26 | GrimsbyvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-10-26 | Crystal PalacevWest BromChampionship · England | 0–2 | Championship · England |
| 1999-10-26 | SwindonvPort ValeChampionship · England | 2–1 | Championship · England |
| 1999-10-26 | WolvesvSheffield UnitedChampionship · England | 1–0 | Championship · England |
| 1999-10-26 | HuddersfieldvBarnsleyChampionship · England | 2–1 | Championship · England |
| 1999-10-26 | CrewevFulhamChampionship · England | 1–1 | Championship · England |
| 1999-10-26 | CharltonvTranmereChampionship · England | 3–2 | Championship · England |
| 1999-10-26 | WalsallvBlackburnChampionship · England | 1–1 | Championship · England |