| 1998-12-28 | GrimsbyvStockportChampionship · England | 1–0 | Championship · England |
| 1998-12-26 | HuddersfieldvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1998-12-19 | GrimsbyvWatfordChampionship · England | 2–1 | Championship · England |
| 1998-12-13 | PortsmouthvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1998-12-05 | TranmerevGrimsbyChampionship · England | 1–2 | Championship · England |
| 1998-12-02 | NorwichvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1998-11-28 | GrimsbyvSwindonChampionship · England | 1–0 | Championship · England |
| 1998-11-21 | BuryvGrimsbyChampionship · England | 1–0 | Championship · England |
| 1998-11-14 | GrimsbyvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1998-11-07 | SunderlandvGrimsbyChampionship · England | 3–1 | Championship · England |
| 1998-10-31 | GrimsbyvCrystal PalaceChampionship · England | 2–0 | Championship · England |
| 1998-10-24 | WolvesvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1998-10-20 | GrimsbyvBristol CityChampionship · England | 2–1 | Championship · England |
| 1998-10-17 | GrimsbyvBradfordChampionship · England | 2–0 | Championship · England |
| 1998-10-03 | QPRvGrimsbyChampionship · England | 1–2 | Championship · England |
| 1998-09-29 | GrimsbyvCreweChampionship · England | 1–1 | Championship · England |
| 1998-09-26 | GrimsbyvPort ValeChampionship · England | 2–2 | Championship · England |
| 1998-09-19 | BirminghamvGrimsbyChampionship · England | 0–1 | Championship · England |
| 1998-09-12 | GrimsbyvBarnsleyChampionship · England | 1–2 | Championship · England |
| 1998-09-08 | Sheffield UnitedvGrimsbyChampionship · England | 3–2 | Championship · England |
| 1998-09-05 | StockportvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1998-08-31 | GrimsbyvWest BromChampionship · England | 5–1 | Championship · England |
| 1998-08-29 | OxfordvGrimsbyChampionship · England | 0–0 | Championship · England |
| 1998-08-22 | GrimsbyvHuddersfieldChampionship · England | 1–0 | Championship · England |
| 1998-08-15 | BoltonvGrimsbyChampionship · England | 2–0 | Championship · England |
| 1998-08-09 | GrimsbyvIpswichChampionship · England | 0–0 | Championship · England |
| 1998-05-02 | GrimsbyvOldhamLeague One · England | 0–2 | League One · England |
| 1998-04-25 | WatfordvGrimsbyLeague One · England | 0–0 | League One · England |
| 1998-04-21 | CarlislevGrimsbyLeague One · England | 0–1 | League One · England |
| 1998-04-13 | GrimsbyvBristol RvsLeague One · England | 1–2 | League One · England |
| 1998-04-10 | WycombevGrimsbyLeague One · England | 1–1 | League One · England |
| 1998-04-07 | GrimsbyvLutonLeague One · England | 0–1 | League One · England |
| 1998-04-04 | GrimsbyvGillinghamLeague One · England | 0–0 | League One · England |
| 1998-03-31 | WrexhamvGrimsbyLeague One · England | 0–0 | League One · England |
| 1998-03-28 | BurnleyvGrimsbyLeague One · England | 2–1 | League One · England |
| 1998-03-24 | GrimsbyvPlymouthLeague One · England | 1–0 | League One · England |
| 1998-03-21 | LutonvGrimsbyLeague One · England | 2–2 | League One · England |
| 1998-03-14 | GrimsbyvWalsallLeague One · England | 3–0 | League One · England |
| 1998-03-07 | SouthendvGrimsbyLeague One · England | 0–1 | League One · England |
| 1998-03-03 | GrimsbyvChesterfieldLeague One · England | 0–0 | League One · England |
| 1998-02-28 | NorthamptonvGrimsbyLeague One · England | 2–1 | League One · England |
| 1998-02-24 | GrimsbyvBlackpoolLeague One · England | 1–0 | League One · England |
| 1998-02-21 | GrimsbyvBournemouthLeague One · England | 2–1 | League One · England |
| 1998-02-14 | WiganvGrimsbyLeague One · England | 0–2 | League One · England |
| 1998-02-07 | MillwallvGrimsbyLeague One · England | 0–1 | League One · England |
| 1998-01-31 | GrimsbyvFulhamLeague One · England | 1–1 | League One · England |
| 1998-01-17 | GrimsbyvBrentfordLeague One · England | 4–0 | League One · England |
| 1998-01-10 | Bristol CityvGrimsbyLeague One · England | 4–1 | League One · England |