| 1999-01-31 | BirminghamvBradfordChampionship · England | 2–1 | Championship · England |
| 1999-01-30 | West BromvGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | IpswichvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-01-30 | QPRvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | HuddersfieldvBristol CityChampionship · England | 2–2 | Championship · England |
| 1999-01-30 | BoltonvNorwichChampionship · England | 2–0 | Championship · England |
| 1999-01-30 | StockportvWolvesChampionship · England | 1–2 | Championship · England |
| 1999-01-30 | WatfordvSunderlandChampionship · England | 2–1 | Championship · England |
| 1999-01-30 | CrewevSheffield UnitedChampionship · England | 1–2 | Championship · England |
| 1999-01-30 | OxfordvBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-01-30 | TranmerevCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-01-30 | SwindonvBuryChampionship · England | 1–1 | Championship · England |
| 1999-01-23 | WatfordvWest BromChampionship · England | 0–2 | Championship · England |
| 1999-01-19 | BradfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-01-17 | SunderlandvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-01-16 | Crystal PalacevStockportChampionship · England | 2–2 | Championship · England |
| 1999-01-16 | BarnsleyvBirminghamChampionship · England | 0–0 | Championship · England |
| 1999-01-16 | PortsmouthvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | Sheffield UnitedvBoltonChampionship · England | 1–2 | Championship · England |
| 1999-01-16 | WolvesvWatfordChampionship · England | 0–0 | Championship · England |
| 1999-01-16 | GrimsbyvOxfordChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | BradfordvCreweChampionship · England | 4–1 | Championship · England |
| 1999-01-16 | Bristol CityvTranmereChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | NorwichvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | BuryvQPRChampionship · England | 1–1 | Championship · England |
| 1999-01-16 | Port ValevSwindonChampionship · England | 0–1 | Championship · England |
| 1999-01-10 | BoltonvCrystal PalaceChampionship · England | 3–0 | Championship · England |
| 1999-01-09 | BirminghamvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-01-09 | HuddersfieldvBuryChampionship · England | 2–2 | Championship · England |
| 1999-01-09 | CrewevNorwichChampionship · England | 3–2 | Championship · England |
| 1999-01-09 | West BromvBarnsleyChampionship · England | 2–0 | Championship · England |
| 1999-01-09 | QPRvSunderlandChampionship · England | 2–2 | Championship · England |
| 1999-01-09 | SwindonvSheffield UnitedChampionship · England | 2–2 | Championship · England |
| 1999-01-09 | WatfordvPortsmouthChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | OxfordvBristol CityChampionship · England | 0–0 | Championship · England |
| 1999-01-09 | IpswichvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1999-01-09 | StockportvBradfordChampionship · England | 1–2 | Championship · England |
| 1999-01-08 | TranmerevWolvesChampionship · England | 1–2 | Championship · England |