| 2000-12-26 | GrimsbyvStockportChampionship · England | 1–1 | Championship · England |
| 2000-12-23 | PrestonvGrimsbyChampionship · England | 1–2 | Championship · England |
| 2000-12-16 | GrimsbyvNorwichChampionship · England | 2–0 | Championship · England |
| 2000-12-13 | WimbledonvGrimsbyChampionship · England | 2–2 | Championship · England |
| 2000-12-09 | TranmerevGrimsbyChampionship · England | 2–0 | Championship · England |
| 2000-12-02 | GrimsbyvCrystal PalaceChampionship · England | 2–2 | Championship · England |
| 2000-11-25 | FulhamvGrimsbyChampionship · England | 2–1 | Championship · England |
| 2000-11-21 | WolvesvGrimsbyChampionship · England | 2–0 | Championship · England |
| 2000-11-18 | Sheffield UnitedvGrimsbyChampionship · England | 3–2 | Championship · England |
| 2000-11-04 | WatfordvGrimsbyChampionship · England | 4–0 | Championship · England |
| 2000-10-29 | GrimsbyvWest BromChampionship · England | 2–0 | Championship · England |
| 2000-10-24 | Crystal PalacevGrimsbyChampionship · England | 0–1 | Championship · England |
| 2000-10-21 | BlackburnvGrimsbyChampionship · England | 2–0 | Championship · England |
| 2000-10-17 | GrimsbyvQPRChampionship · England | 3–1 | Championship · England |
| 2000-10-14 | GrimsbyvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 2000-09-30 | BarnsleyvGrimsbyChampionship · England | 2–0 | Championship · England |
| 2000-09-23 | GrimsbyvNott'm ForestChampionship · England | 0–2 | Championship · England |
| 2000-09-16 | BurnleyvGrimsbyChampionship · England | 1–1 | Championship · England |
| 2000-09-12 | GrimsbyvBoltonChampionship · England | 0–1 | Championship · England |
| 2000-09-09 | GrimsbyvGillinghamChampionship · England | 1–0 | Championship · England |
| 2000-08-29 | CrewevGrimsbyChampionship · England | 2–0 | Championship · England |
| 2000-08-26 | GrimsbyvSheffield WedsChampionship · England | 0–1 | Championship · England |
| 2000-08-19 | PortsmouthvGrimsbyChampionship · England | 1–1 | Championship · England |
| 2000-08-12 | GrimsbyvPrestonChampionship · England | 1–2 | Championship · England |
| 2000-05-07 | BirminghamvGrimsbyChampionship · England | 0–0 | Championship · England |
| 2000-04-29 | GrimsbyvTranmereChampionship · England | 1–2 | Championship · England |
| 2000-04-24 | West BromvGrimsbyChampionship · England | 2–1 | Championship · England |
| 2000-04-22 | GrimsbyvBlackburnChampionship · England | 0–0 | Championship · England |
| 2000-04-15 | GrimsbyvMan CityChampionship · England | 1–1 | Championship · England |
| 2000-04-08 | Sheffield UnitedvGrimsbyChampionship · England | 0–0 | Championship · England |
| 2000-04-01 | GrimsbyvHuddersfieldChampionship · England | 0–0 | Championship · England |
| 2000-03-27 | BarnsleyvGrimsbyChampionship · England | 3–0 | Championship · England |
| 2000-03-22 | CharltonvGrimsbyChampionship · England | 4–0 | Championship · England |
| 2000-03-18 | GrimsbyvBoltonChampionship · England | 0–1 | Championship · England |
| 2000-03-11 | QPRvGrimsbyChampionship · England | 1–0 | Championship · England |
| 2000-03-07 | GrimsbyvWolvesChampionship · England | 1–0 | Championship · England |
| 2000-03-04 | WalsallvGrimsbyChampionship · England | 1–0 | Championship · England |
| 2000-02-26 | GrimsbyvCrystal PalaceChampionship · England | 1–0 | Championship · England |
| 2000-02-19 | NorwichvGrimsbyChampionship · England | 3–0 | Championship · England |
| 2000-02-12 | GrimsbyvPort ValeChampionship · England | 2–0 | Championship · England |
| 2000-02-05 | SwindonvGrimsbyChampionship · England | 0–1 | Championship · England |
| 2000-01-29 | GrimsbyvCreweChampionship · England | 1–1 | Championship · England |
| 2000-01-22 | FulhamvGrimsbyChampionship · England | 0–1 | Championship · England |
| 2000-01-15 | GrimsbyvNott'm ForestChampionship · England | 4–3 | Championship · England |
| 2000-01-03 | GrimsbyvSheffield UnitedChampionship · England | 2–2 | Championship · England |