| 1999-12-28 | BarnsleyvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-12-18 | PortsmouthvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-12-04 | Port ValevBlackburnChampionship · England | 0–0 | Championship · England |
| 1999-11-27 | CharltonvPort ValeChampionship · England | 2–2 | Championship · England |
| 1999-11-23 | Sheffield UnitedvPort ValeChampionship · England | 1–3 | Championship · England |
| 1999-11-20 | Port ValevCrystal PalaceChampionship · England | 2–2 | Championship · England |
| 1999-11-12 | WalsallvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-11-05 | Port ValevCreweChampionship · England | 1–0 | Championship · England |
| 1999-10-30 | Port ValevMan CityChampionship · England | 1–2 | Championship · England |
| 1999-10-26 | SwindonvPort ValeChampionship · England | 2–1 | Championship · England |
| 1999-10-23 | WolvesvPort ValeChampionship · England | 2–2 | Championship · England |
| 1999-10-19 | Port ValevNott'm ForestChampionship · England | 0–2 | Championship · England |
| 1999-10-16 | Port ValevNorwichChampionship · England | 0–1 | Championship · England |
| 1999-10-09 | HuddersfieldvPort ValeChampionship · England | 2–2 | Championship · England |
| 1999-10-02 | Man CityvPort ValeChampionship · England | 2–1 | Championship · England |
| 1999-09-25 | Port ValevSwindonChampionship · England | 2–0 | Championship · England |
| 1999-09-18 | StockportvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-09-11 | Port ValevFulhamChampionship · England | 0–2 | Championship · England |
| 1999-09-05 | Port ValevGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-08-31 | QPRvPort ValeChampionship · England | 3–2 | Championship · England |
| 1999-08-28 | Port ValevTranmereChampionship · England | 1–0 | Championship · England |
| 1999-08-21 | BirminghamvPort ValeChampionship · England | 4–2 | Championship · England |
| 1999-08-14 | Port ValevWest BromChampionship · England | 1–2 | Championship · England |
| 1999-08-07 | BlackburnvPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-05-09 | BuryvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-05-01 | Port ValevQPRChampionship · England | 2–0 | Championship · England |
| 1999-04-27 | Port ValevWatfordChampionship · England | 1–2 | Championship · England |
| 1999-04-24 | TranmerevPort ValeChampionship · England | 1–1 | Championship · England |
| 1999-04-17 | Port ValevOxfordChampionship · England | 1–0 | Championship · England |
| 1999-04-13 | Port ValevBradfordChampionship · England | 1–1 | Championship · England |
| 1999-04-10 | CrewevPort ValeChampionship · England | 0–0 | Championship · England |
| 1999-04-05 | Port ValevBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-04-03 | Bristol CityvPort ValeChampionship · England | 2–0 | Championship · England |
| 1999-03-23 | Port ValevGrimsbyChampionship · England | 0–1 | Championship · England |
| 1999-03-20 | Sheffield UnitedvPort ValeChampionship · England | 3–0 | Championship · England |
| 1999-03-13 | Port ValevStockportChampionship · England | 1–1 | Championship · England |
| 1999-03-09 | NorwichvPort ValeChampionship · England | 3–4 | Championship · England |
| 1999-02-27 | PortsmouthvPort ValeChampionship · England | 4–0 | Championship · England |
| 1999-02-20 | Port ValevCrystal PalaceChampionship · England | 1–0 | Championship · England |
| 1999-02-13 | WolvesvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-02-06 | Port ValevHuddersfieldChampionship · England | 2–0 | Championship · England |
| 1999-01-30 | IpswichvPort ValeChampionship · England | 1–0 | Championship · England |
| 1999-01-16 | Port ValevSwindonChampionship · England | 0–1 | Championship · England |
| 1999-01-09 | BirminghamvPort ValeChampionship · England | 1–0 | Championship · England |