| 1999-12-28 | Crystal PalacevWalsallChampionship · England | 3–2 | Championship · England |
| 1999-12-26 | CharltonvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-12-18 | Crystal PalacevFulhamChampionship · England | 0–0 | Championship · England |
| 1999-12-07 | Crystal PalacevIpswichChampionship · England | 2–2 | Championship · England |
| 1999-12-04 | CrewevCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-11-27 | Crystal PalacevNott'm ForestChampionship · England | 2–0 | Championship · England |
| 1999-11-23 | Crystal PalacevNorwichChampionship · England | 1–0 | Championship · England |
| 1999-11-20 | Port ValevCrystal PalaceChampionship · England | 2–2 | Championship · England |
| 1999-11-14 | Crystal PalacevQPRChampionship · England | 3–0 | Championship · England |
| 1999-11-06 | BoltonvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-10-30 | PortsmouthvCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-10-26 | Crystal PalacevWest BromChampionship · England | 0–2 | Championship · England |
| 1999-10-23 | Crystal PalacevTranmereChampionship · England | 2–2 | Championship · England |
| 1999-10-20 | BlackburnvCrystal PalaceChampionship · England | 1–1 | Championship · England |
| 1999-10-16 | BirminghamvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1999-10-02 | Crystal PalacevPortsmouthChampionship · England | 4–0 | Championship · England |
| 1999-09-28 | Crystal PalacevWolvesChampionship · England | 1–1 | Championship · England |
| 1999-09-25 | West BromvCrystal PalaceChampionship · England | 0–0 | Championship · England |
| 1999-09-18 | Crystal PalacevGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-09-11 | Man CityvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-09-04 | Sheffield UnitedvCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-08-28 | HuddersfieldvCrystal PalaceChampionship · England | 7–1 | Championship · England |
| 1999-08-21 | Crystal PalacevSwindonChampionship · England | 1–2 | Championship · England |
| 1999-08-14 | BarnsleyvCrystal PalaceChampionship · England | 2–3 | Championship · England |
| 1999-08-07 | Crystal PalacevCreweChampionship · England | 1–1 | Championship · England |
| 1999-05-09 | QPRvCrystal PalaceChampionship · England | 6–0 | Championship · England |
| 1999-05-01 | Crystal PalacevHuddersfieldChampionship · England | 2–2 | Championship · England |
| 1999-04-24 | WatfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-04-17 | Crystal PalacevSwindonChampionship · England | 0–1 | Championship · England |
| 1999-04-10 | WolvesvCrystal PalaceChampionship · England | 0–0 | Championship · England |
| 1999-04-05 | Crystal PalacevSunderlandChampionship · England | 1–1 | Championship · England |
| 1999-04-03 | NorwichvCrystal PalaceChampionship · England | 0–1 | Championship · England |
| 1999-03-28 | Crystal PalacevBradfordChampionship · England | 1–0 | Championship · England |
| 1999-03-20 | Crystal PalacevGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-03-13 | PortsmouthvCrystal PalaceChampionship · England | 1–1 | Championship · England |
| 1999-03-09 | Crystal PalacevIpswichChampionship · England | 3–2 | Championship · England |
| 1999-03-06 | BuryvCrystal PalaceChampionship · England | 0–0 | Championship · England |
| 1999-03-02 | Sheffield UnitedvCrystal PalaceChampionship · England | 1–1 | Championship · England |
| 1999-02-28 | Crystal PalacevBarnsleyChampionship · England | 1–0 | Championship · England |
| 1999-02-20 | Port ValevCrystal PalaceChampionship · England | 1–0 | Championship · England |
| 1999-02-13 | Crystal PalacevCreweChampionship · England | 1–1 | Championship · England |
| 1999-02-06 | Crystal PalacevBirminghamChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | TranmerevCrystal PalaceChampionship · England | 3–1 | Championship · England |
| 1999-01-19 | BradfordvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-01-16 | Crystal PalacevStockportChampionship · England | 2–2 | Championship · England |
| 1999-01-10 | BoltonvCrystal PalaceChampionship · England | 3–0 | Championship · England |