| 1999-12-28 | QPRvCreweChampionship · England | 1–0 | Championship · England |
| 1999-12-26 | CrewevHuddersfieldChampionship · England | 1–1 | Championship · England |
| 1999-12-18 | Nott'm ForestvCreweChampionship · England | 1–0 | Championship · England |
| 1999-12-14 | CrewevWolvesChampionship · England | 1–0 | Championship · England |
| 1999-12-07 | CrewevWest BromChampionship · England | 2–0 | Championship · England |
| 1999-12-04 | CrewevCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-11-27 | IpswichvCreweChampionship · England | 2–1 | Championship · England |
| 1999-11-23 | CrewevBlackburnChampionship · England | 0–0 | Championship · England |
| 1999-11-20 | PortsmouthvCreweChampionship · England | 0–2 | Championship · England |
| 1999-11-05 | Port ValevCreweChampionship · England | 1–0 | Championship · England |
| 1999-11-02 | CrewevCharltonChampionship · England | 0–2 | Championship · England |
| 1999-10-30 | TranmerevCreweChampionship · England | 2–0 | Championship · England |
| 1999-10-26 | CrewevFulhamChampionship · England | 1–1 | Championship · England |
| 1999-10-23 | CrewevBarnsleyChampionship · England | 0–1 | Championship · England |
| 1999-10-19 | BoltonvCreweChampionship · England | 2–2 | Championship · England |
| 1999-10-16 | StockportvCreweChampionship · England | 2–1 | Championship · England |
| 1999-10-09 | CrewevSheffield UnitedChampionship · England | 1–0 | Championship · England |
| 1999-10-03 | CrewevTranmereChampionship · England | 0–2 | Championship · England |
| 1999-09-25 | FulhamvCreweChampionship · England | 3–0 | Championship · England |
| 1999-09-18 | CrewevSwindonChampionship · England | 2–1 | Championship · England |
| 1999-09-11 | NorwichvCreweChampionship · England | 2–1 | Championship · England |
| 1999-08-30 | BirminghamvCreweChampionship · England | 5–1 | Championship · England |
| 1999-08-27 | CrewevGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-08-21 | WalsallvCreweChampionship · England | 1–4 | Championship · England |
| 1999-08-07 | Crystal PalacevCreweChampionship · England | 1–1 | Championship · England |
| 1999-05-09 | HuddersfieldvCreweChampionship · England | 0–0 | Championship · England |
| 1999-05-01 | CrewevPortsmouthChampionship · England | 3–1 | Championship · England |
| 1999-04-27 | CrewevBristol CityChampionship · England | 1–0 | Championship · England |
| 1999-04-24 | IpswichvCreweChampionship · England | 1–2 | Championship · England |
| 1999-04-17 | CrewevWatfordChampionship · England | 0–1 | Championship · England |
| 1999-04-10 | CrewevPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-04-05 | West BromvCreweChampionship · England | 1–5 | Championship · England |
| 1999-04-02 | CrewevBirminghamChampionship · England | 0–0 | Championship · England |
| 1999-03-30 | WolvesvCreweChampionship · England | 3–0 | Championship · England |
| 1999-03-26 | TranmerevCreweChampionship · England | 3–0 | Championship · England |
| 1999-03-20 | CrewevOxfordChampionship · England | 3–1 | Championship · England |
| 1999-03-16 | CrewevGrimsbyChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | SwindonvCreweChampionship · England | 1–2 | Championship · England |
| 1999-02-27 | BoltonvCreweChampionship · England | 1–3 | Championship · England |
| 1999-02-20 | CrewevStockportChampionship · England | 0–2 | Championship · England |
| 1999-02-13 | Crystal PalacevCreweChampionship · England | 1–1 | Championship · England |
| 1999-02-06 | BarnsleyvCreweChampionship · England | 2–2 | Championship · England |
| 1999-01-30 | CrewevSheffield UnitedChampionship · England | 1–2 | Championship · England |
| 1999-01-16 | BradfordvCreweChampionship · England | 4–1 | Championship · England |
| 1999-01-09 | CrewevNorwichChampionship · England | 3–2 | Championship · England |