| 1999-08-30 | Man CityvNott'm ForestChampionship · England | 1–0 | Championship · England |
| 1999-08-30 | West BromvFulhamChampionship · England | 0–0 | Championship · England |
| 1999-08-30 | TranmerevSheffield UnitedChampionship · England | 1–3 | Championship · England |
| 1999-08-30 | IpswichvBarnsleyChampionship · England | 6–1 | Championship · England |
| 1999-08-30 | GrimsbyvSwindonChampionship · England | 1–0 | Championship · England |
| 1999-08-30 | BirminghamvCreweChampionship · England | 5–1 | Championship · England |
| 1999-08-30 | WalsallvNorwichChampionship · England | 2–2 | Championship · England |
| 1999-08-28 | Sheffield UnitedvIpswichChampionship · England | 2–2 | Championship · England |
| 1999-08-28 | FulhamvCharltonChampionship · England | 2–1 | Championship · England |
| 1999-08-28 | HuddersfieldvCrystal PalaceChampionship · England | 7–1 | Championship · England |
| 1999-08-28 | Nott'm ForestvQPRChampionship · England | 1–1 | Championship · England |
| 1999-08-28 | BoltonvMan CityChampionship · England | 0–1 | Championship · England |
| 1999-08-28 | SwindonvWest BromChampionship · England | 1–2 | Championship · England |
| 1999-08-28 | NorwichvBlackburnChampionship · England | 0–2 | Championship · England |
| 1999-08-28 | Port ValevTranmereChampionship · England | 1–0 | Championship · England |
| 1999-08-28 | BarnsleyvPortsmouthChampionship · England | 6–0 | Championship · England |
| 1999-08-28 | WolvesvWalsallChampionship · England | 1–2 | Championship · England |
| 1999-08-27 | CrewevGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-08-27 | StockportvBirminghamChampionship · England | 2–0 | Championship · England |
| 1999-08-21 | Man CityvSheffield UnitedChampionship · England | 6–0 | Championship · England |
| 1999-08-21 | BirminghamvPort ValeChampionship · England | 4–2 | Championship · England |
| 1999-08-21 | WalsallvCreweChampionship · England | 1–4 | Championship · England |
| 1999-08-21 | BlackburnvBarnsleyChampionship · England | 1–2 | Championship · England |
| 1999-08-21 | TranmerevHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-08-21 | IpswichvBoltonChampionship · England | 1–0 | Championship · England |
| 1999-08-21 | PortsmouthvStockportChampionship · England | 2–0 | Championship · England |
| 1999-08-21 | GrimsbyvFulhamChampionship · England | 1–1 | Championship · England |
| 1999-08-21 | QPRvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-08-21 | CharltonvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-08-21 | Crystal PalacevSwindonChampionship · England | 1–2 | Championship · England |
| 1999-08-20 | West BromvNott'm ForestChampionship · England | 1–1 | Championship · England |
| 1999-08-15 | SwindonvIpswichChampionship · England | 1–4 | Championship · England |
| 1999-08-14 | Sheffield UnitedvWalsallChampionship · England | 1–1 | Championship · England |
| 1999-08-14 | Port ValevWest BromChampionship · England | 1–2 | Championship · England |
| 1999-08-14 | NorwichvBirminghamChampionship · England | 0–1 | Championship · England |
| 1999-08-14 | StockportvTranmereChampionship · England | 2–1 | Championship · England |
| 1999-08-14 | Nott'm ForestvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-08-14 | FulhamvMan CityChampionship · England | 0–0 | Championship · England |
| 1999-08-14 | WolvesvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-08-14 | BarnsleyvCrystal PalaceChampionship · England | 2–3 | Championship · England |
| 1999-08-14 | BoltonvQPRChampionship · England | 2–1 | Championship · England |
| 1999-08-13 | HuddersfieldvBlackburnChampionship · England | 3–2 | Championship · England |
| 1999-08-08 | Man CityvWolvesChampionship · England | 0–1 | Championship · England |
| 1999-08-07 | TranmerevBoltonChampionship · England | 0–0 | Championship · England |
| 1999-08-07 | GrimsbyvStockportChampionship · England | 0–1 | Championship · England |
| 1999-08-07 | CharltonvBarnsleyChampionship · England | 3–1 | Championship · England |
| 1999-08-07 | IpswichvNott'm ForestChampionship · England | 3–1 | Championship · England |
| 1999-08-07 | QPRvHuddersfieldChampionship · England | 3–1 | Championship · England |
| 1999-08-07 | WalsallvSwindonChampionship · England | 0–0 | Championship · England |
| 1999-08-07 | BlackburnvPort ValeChampionship · England | 0–0 | Championship · England |