| 1999-12-28 | HuddersfieldvCharltonChampionship · England | 1–2 | Championship · England |
| 1999-12-26 | CharltonvCrystal PalaceChampionship · England | 2–1 | Championship · England |
| 1999-12-18 | QPRvCharltonChampionship · England | 0–0 | Championship · England |
| 1999-12-04 | BarnsleyvCharltonChampionship · England | 1–1 | Championship · England |
| 1999-11-30 | CharltonvBlackburnChampionship · England | 1–2 | Championship · England |
| 1999-11-27 | CharltonvPort ValeChampionship · England | 2–2 | Championship · England |
| 1999-11-23 | SwindonvCharltonChampionship · England | 1–2 | Championship · England |
| 1999-11-20 | CharltonvMan CityChampionship · England | 0–1 | Championship · England |
| 1999-11-12 | GrimsbyvCharltonChampionship · England | 2–5 | Championship · England |
| 1999-11-06 | CharltonvWalsallChampionship · England | 2–1 | Championship · England |
| 1999-11-02 | CrewevCharltonChampionship · England | 0–2 | Championship · England |
| 1999-10-30 | BirminghamvCharltonChampionship · England | 1–0 | Championship · England |
| 1999-10-26 | CharltonvTranmereChampionship · England | 3–2 | Championship · England |
| 1999-10-23 | CharltonvWest BromChampionship · England | 0–0 | Championship · England |
| 1999-10-19 | IpswichvCharltonChampionship · England | 4–2 | Championship · England |
| 1999-10-16 | PortsmouthvCharltonChampionship · England | 0–2 | Championship · England |
| 1999-10-02 | CharltonvBirminghamChampionship · England | 1–0 | Championship · England |
| 1999-09-28 | CharltonvStockportChampionship · England | 4–0 | Championship · England |
| 1999-09-25 | TranmerevCharltonChampionship · England | 2–2 | Championship · England |
| 1999-09-18 | Sheffield UnitedvCharltonChampionship · England | 1–2 | Championship · England |
| 1999-09-11 | CharltonvBoltonChampionship · England | 2–1 | Championship · England |
| 1999-08-28 | FulhamvCharltonChampionship · England | 2–1 | Championship · England |
| 1999-08-21 | CharltonvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-08-07 | CharltonvBarnsleyChampionship · England | 3–1 | Championship · England |
| 1999-05-16 | CharltonvSheffield WedsPremier League · England | 0–1 | Premier League · England |
| 1999-05-08 | Aston VillavCharltonPremier League · England | 3–4 | Premier League · England |
| 1999-05-01 | CharltonvBlackburnPremier League · England | 0–0 | Premier League · England |
| 1999-04-24 | EvertonvCharltonPremier League · England | 4–1 | Premier League · England |
| 1999-04-20 | CharltonvTottenhamPremier League · England | 1–4 | Premier League · England |
| 1999-04-17 | CharltonvLeedsPremier League · England | 1–1 | Premier League · England |
| 1999-04-10 | MiddlesbroughvCharltonPremier League · England | 2–0 | Premier League · England |
| 1999-04-05 | West HamvCharltonPremier League · England | 0–1 | Premier League · England |
| 1999-04-03 | CharltonvChelseaPremier League · England | 0–1 | Premier League · England |
| 1999-03-13 | LeicestervCharltonPremier League · England | 1–1 | Premier League · England |
| 1999-03-06 | CoventryvCharltonPremier League · England | 2–1 | Premier League · England |
| 1999-02-27 | CharltonvNott'm ForestPremier League · England | 0–0 | Premier League · England |
| 1999-02-20 | DerbyvCharltonPremier League · England | 0–2 | Premier League · England |
| 1999-02-13 | CharltonvLiverpoolPremier League · England | 1–0 | Premier League · England |
| 1999-02-08 | CharltonvWimbledonPremier League · England | 2–0 | Premier League · England |
| 1999-01-31 | CharltonvMan UnitedPremier League · England | 0–1 | Premier League · England |
| 1999-01-17 | CharltonvNewcastlePremier League · England | 2–2 | Premier League · England |
| 1999-01-09 | SouthamptonvCharltonPremier League · England | 3–1 | Premier League · England |