| 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 |
| 1999-12-28 | Man CityvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-12-26 | GrimsbyvBarnsleyChampionship · England | 0–3 | Championship · England |
| 1999-12-18 | HuddersfieldvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-12-14 | GrimsbyvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-12-04 | StockportvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-11-28 | GrimsbyvNorwichChampionship · England | 2–1 | Championship · England |
| 1999-11-23 | GrimsbyvQPRChampionship · England | 2–1 | Championship · England |
| 1999-11-20 | BoltonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-11-12 | GrimsbyvCharltonChampionship · England | 2–5 | Championship · England |
| 1999-11-06 | WolvesvGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-10-30 | IpswichvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-10-26 | GrimsbyvPortsmouthChampionship · England | 1–0 | Championship · England |
| 1999-10-23 | GrimsbyvBirminghamChampionship · England | 1–1 | Championship · England |
| 1999-10-19 | TranmerevGrimsbyChampionship · England | 3–2 | Championship · England |
| 1999-10-16 | BlackburnvGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-10-02 | GrimsbyvIpswichChampionship · England | 2–1 | Championship · England |
| 1999-09-25 | PortsmouthvGrimsbyChampionship · England | 1–2 | Championship · England |
| 1999-09-18 | Crystal PalacevGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-09-11 | GrimsbyvWalsallChampionship · England | 1–0 | Championship · England |
| 1999-09-05 | Port ValevGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-08-30 | GrimsbyvSwindonChampionship · England | 1–0 | Championship · England |
| 1999-08-27 | CrewevGrimsbyChampionship · England | 1–1 | Championship · England |
| 1999-08-21 | GrimsbyvFulhamChampionship · England | 1–1 | Championship · England |
| 1999-08-14 | Nott'm ForestvGrimsbyChampionship · England | 2–1 | Championship · England |
| 1999-08-07 | GrimsbyvStockportChampionship · England | 0–1 | Championship · England |
| 1999-05-09 | WatfordvGrimsbyChampionship · England | 1–0 | Championship · England |
| 1999-05-04 | GrimsbyvWolvesChampionship · England | 0–0 | Championship · England |
| 1999-05-01 | GrimsbyvTranmereChampionship · England | 1–0 | Championship · England |
| 1999-04-24 | SwindonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1999-04-20 | GrimsbyvSheffield UnitedChampionship · England | 1–2 | Championship · England |
| 1999-04-17 | GrimsbyvBuryChampionship · England | 0–0 | Championship · England |
| 1999-04-13 | GrimsbyvQPRChampionship · England | 1–0 | Championship · England |
| 1999-04-10 | Bristol CityvGrimsbyChampionship · England | 4–1 | Championship · England |
| 1999-04-05 | GrimsbyvNorwichChampionship · England | 0–1 | Championship · England |
| 1999-04-03 | BradfordvGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-03-23 | Port ValevGrimsbyChampionship · England | 0–1 | Championship · England |
| 1999-03-20 | Crystal PalacevGrimsbyChampionship · England | 3–1 | Championship · England |
| 1999-03-16 | CrewevGrimsbyChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | GrimsbyvSunderlandChampionship · England | 0–2 | Championship · England |
| 1999-02-27 | GrimsbyvBirminghamChampionship · England | 0–3 | Championship · England |
| 1999-02-20 | BarnsleyvGrimsbyChampionship · England | 0–0 | Championship · England |