| 2000-12-26 | GillinghamvCrystal PalaceChampionship · England | 4–1 | Championship · England |
| 2000-12-22 | StockportvGillinghamChampionship · England | 2–2 | Championship · England |
| 2000-12-16 | GillinghamvPrestonChampionship · England | 4–0 | Championship · England |
| 2000-12-09 | NorwichvGillinghamChampionship · England | 1–0 | Championship · England |
| 2000-12-02 | GillinghamvBirminghamChampionship · England | 1–2 | Championship · England |
| 2000-11-25 | BlackburnvGillinghamChampionship · England | 1–2 | Championship · England |
| 2000-11-18 | West BromvGillinghamChampionship · England | 3–1 | Championship · England |
| 2000-11-12 | GillinghamvNott'm ForestChampionship · England | 1–3 | Championship · England |
| 2000-11-04 | Sheffield UnitedvGillinghamChampionship · England | 1–2 | Championship · England |
| 2000-10-28 | GillinghamvCreweChampionship · England | 0–1 | Championship · England |
| 2000-10-25 | BirminghamvGillinghamChampionship · England | 1–0 | Championship · England |
| 2000-10-21 | GillinghamvBarnsleyChampionship · England | 0–0 | Championship · England |
| 2000-10-17 | WatfordvGillinghamChampionship · England | 0–0 | Championship · England |
| 2000-10-14 | WimbledonvGillinghamChampionship · England | 4–4 | Championship · England |
| 2000-10-06 | GillinghamvBoltonChampionship · England | 2–2 | Championship · England |
| 2000-09-30 | GillinghamvSheffield WedsChampionship · England | 2–0 | Championship · England |
| 2000-09-23 | FulhamvGillinghamChampionship · England | 3–0 | Championship · England |
| 2000-09-16 | GillinghamvHuddersfieldChampionship · England | 2–1 | Championship · England |
| 2000-09-13 | QPRvGillinghamChampionship · England | 2–2 | Championship · England |
| 2000-09-09 | GrimsbyvGillinghamChampionship · England | 1–0 | Championship · England |
| 2000-09-02 | GillinghamvWolvesChampionship · England | 1–0 | Championship · England |
| 2000-08-28 | BurnleyvGillinghamChampionship · England | 1–1 | Championship · England |
| 2000-08-25 | GillinghamvPortsmouthChampionship · England | 1–1 | Championship · England |
| 2000-08-19 | TranmerevGillinghamChampionship · England | 3–2 | Championship · England |
| 2000-08-12 | GillinghamvStockportChampionship · England | 1–3 | Championship · England |
| 2000-05-06 | WrexhamvGillinghamLeague One · England | 1–0 | League One · England |
| 2000-05-02 | GillinghamvCardiffLeague One · England | 4–1 | League One · England |
| 2000-04-29 | GillinghamvBrentfordLeague One · England | 2–0 | League One · England |
| 2000-04-24 | MillwallvGillinghamLeague One · England | 2–2 | League One · England |
| 2000-04-22 | GillinghamvLutonLeague One · England | 2–0 | League One · England |
| 2000-04-18 | BurnleyvGillinghamLeague One · England | 0–3 | League One · England |
| 2000-04-15 | GillinghamvWiganLeague One · England | 2–1 | League One · England |
| 2000-04-07 | ReadingvGillinghamLeague One · England | 2–2 | League One · England |
| 2000-04-01 | GillinghamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2000-03-28 | WycombevGillinghamLeague One · England | 1–0 | League One · England |
| 2000-03-25 | ColchestervGillinghamLeague One · England | 2–1 | League One · England |
| 2000-03-21 | BournemouthvGillinghamLeague One · England | 0–1 | League One · England |
| 2000-03-18 | GillinghamvScunthorpeLeague One · England | 3–1 | League One · England |
| 2000-03-14 | GillinghamvBurnleyLeague One · England | 2–2 | League One · England |
| 2000-03-11 | Bristol CityvGillinghamLeague One · England | 0–1 | League One · England |
| 2000-03-07 | GillinghamvNotts CountyLeague One · England | 0–1 | League One · England |
| 2000-03-04 | GillinghamvOxfordLeague One · England | 1–0 | League One · England |
| 2000-02-26 | PrestonvGillinghamLeague One · England | 0–2 | League One · England |
| 2000-02-12 | OldhamvGillinghamLeague One · England | 1–3 | League One · England |
| 2000-02-05 | GillinghamvStokeLeague One · England | 3–0 | League One · England |
| 2000-02-01 | ChesterfieldvGillinghamLeague One · England | 0–0 | League One · England |
| 2000-01-22 | GillinghamvBlackpoolLeague One · England | 1–3 | League One · England |
| 2000-01-15 | Bristol RvsvGillinghamLeague One · England | 2–1 | League One · England |
| 2000-01-03 | GillinghamvReadingLeague One · England | 2–2 | League One · England |