| 1999-12-28 | HuddersfieldvCharltonChampionship · England | 1–2 | Championship · England |
| 1999-12-28 | PortsmouthvBlackburnChampionship · England | 1–2 | Championship · England |
| 1999-12-28 | BoltonvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-12-28 | TranmerevSwindonChampionship · England | 3–1 | Championship · England |
| 1999-12-28 | Nott'm ForestvBirminghamChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | Sheffield UnitedvFulhamChampionship · England | 2–0 | Championship · England |
| 1999-12-28 | Man CityvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-12-28 | IpswichvStockportChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | WolvesvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | Crystal PalacevWalsallChampionship · England | 3–2 | Championship · England |
| 1999-12-28 | QPRvCreweChampionship · England | 1–0 | Championship · England |
| 1999-12-28 | BarnsleyvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-12-26 | BirminghamvSheffield UnitedChampionship · England | 0–2 | Championship · England |
| 1999-12-26 | CrewevHuddersfieldChampionship · England | 1–1 | Championship · England |
| 1999-12-26 | SwindonvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-12-26 | StockportvWolvesChampionship · England | 3–2 | Championship · England |
| 1999-12-26 | West BromvMan CityChampionship · England | 0–2 | Championship · England |
| 1999-12-26 | WalsallvTranmereChampionship · England | 1–2 | Championship · England |
| 1999-12-26 | NorwichvQPRChampionship · England | 2–1 | Championship · England |
| 1999-12-26 | FulhamvIpswichChampionship · England | 0–0 | Championship · England |
| 1999-12-26 | BlackburnvNott'm ForestChampionship · England | 2–1 | Championship · England |
| 1999-12-26 | GrimsbyvBarnsleyChampionship · England | 0–3 | Championship · England |
| 1999-12-26 | CharltonvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-12-19 | Sheffield UnitedvBlackburnChampionship · England | 2–1 | Championship · England |
| 1999-12-18 | Man CityvSwindonChampionship · England | 3–0 | Championship · England |
| 1999-12-18 | PortsmouthvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-12-18 | Crystal PalacevFulhamChampionship · England | 0–0 | Championship · England |
| 1999-12-18 | HuddersfieldvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-12-18 | BoltonvStockportChampionship · England | 0–1 | Championship · England |
| 1999-12-18 | QPRvCharltonChampionship · England | 0–0 | Championship · England |
| 1999-12-18 | IpswichvWest BromChampionship · England | 3–1 | Championship · England |
| 1999-12-18 | Nott'm ForestvCreweChampionship · England | 1–0 | Championship · England |
| 1999-12-18 | BarnsleyvWalsallChampionship · England | 3–2 | Championship · England |
| 1999-12-17 | WolvesvBirminghamChampionship · England | 2–1 | Championship · England |
| 1999-12-17 | TranmerevNorwichChampionship · England | 1–2 | Championship · England |
| 1999-12-15 | Nott'm ForestvFulhamChampionship · England | 0–0 | Championship · England |
| 1999-12-14 | CrewevWolvesChampionship · England | 1–0 | Championship · England |
| 1999-12-14 | GrimsbyvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-12-07 | BlackburnvBoltonChampionship · England | 3–1 | Championship · England |
| 1999-12-07 | CrewevWest BromChampionship · England | 2–0 | Championship · England |
| 1999-12-07 | Man CityvStockportChampionship · England | 1–2 | Championship · England |
| 1999-12-07 | Crystal PalacevIpswichChampionship · England | 2–2 | Championship · England |
| 1999-12-05 | Nott'm ForestvIpswichChampionship · England | 0–1 | Championship · England |
| 1999-12-04 | StockportvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-12-04 | HuddersfieldvQPRChampionship · England | 1–0 | Championship · England |
| 1999-12-04 | BarnsleyvCharltonChampionship · England | 1–1 | Championship · England |
| 1999-12-04 | Sheffield UnitedvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-12-04 | SwindonvWalsallChampionship · England | 1–1 | Championship · England |
| 1999-12-04 | BoltonvTranmereChampionship · England | 2–3 | Championship · England |
| 1999-12-04 | Port ValevBlackburnChampionship · England | 0–0 | Championship · England |