| 2008-12-28 | AccringtonvGrimsbyLeague Two · England | 3–1 | League Two · England |
| 2008-12-26 | GrimsbyvNotts CountyLeague Two · England | 0–1 | League Two · England |
| 2008-12-20 | AldershotvGrimsbyLeague Two · England | 2–2 | League Two · England |
| 2008-12-13 | GrimsbyvShrewsburyLeague Two · England | 1–0 | League Two · England |
| 2008-12-06 | Port ValevGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2008-11-25 | MacclesfieldvGrimsbyLeague Two · England | 1–0 | League Two · England |
| 2008-11-21 | GrimsbyvBournemouthLeague Two · England | 3–3 | League Two · England |
| 2008-11-15 | BuryvGrimsbyLeague Two · England | 0–2 | League Two · England |
| 2008-11-01 | GrimsbyvDarlingtonLeague Two · England | 1–2 | League Two · England |
| 2008-10-28 | Dag and RedvGrimsbyLeague Two · England | 4–0 | League Two · England |
| 2008-10-24 | GrimsbyvBradfordLeague Two · England | 1–3 | League Two · England |
| 2008-10-21 | GrimsbyvLutonLeague Two · England | 2–2 | League Two · England |
| 2008-10-18 | ExetervGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2008-10-11 | GrimsbyvWycombeLeague Two · England | 1–1 | League Two · England |
| 2008-10-04 | RotherhamvGrimsbyLeague Two · England | 4–1 | League Two · England |
| 2008-09-27 | GrimsbyvBarnetLeague Two · England | 0–1 | League Two · England |
| 2008-09-20 | MorecambevGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2008-09-13 | GrimsbyvChesterLeague Two · England | 1–3 | League Two · England |
| 2008-09-06 | GillinghamvGrimsbyLeague Two · England | 3–0 | League Two · England |
| 2008-08-30 | LincolnvGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2008-08-23 | GrimsbyvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2008-08-16 | BrentfordvGrimsbyLeague Two · England | 4–0 | League Two · England |
| 2008-08-09 | GrimsbyvRochdaleLeague Two · England | 0–0 | League Two · England |
| 2008-05-03 | HerefordvGrimsbyLeague Two · England | 2–0 | League Two · England |
| 2008-04-26 | GrimsbyvPeterboroLeague Two · England | 1–4 | League Two · England |
| 2008-04-19 | BradfordvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2008-04-15 | GrimsbyvWycombeLeague Two · England | 0–1 | League Two · England |
| 2008-04-12 | GrimsbyvRotherhamLeague Two · England | 0–1 | League Two · England |
| 2008-04-05 | RochdalevGrimsbyLeague Two · England | 3–1 | League Two · England |
| 2008-03-24 | GrimsbyvBrentfordLeague Two · England | 1–2 | League Two · England |
| 2008-03-22 | MansfieldvGrimsbyLeague Two · England | 1–2 | League Two · England |
| 2008-03-15 | DarlingtonvGrimsbyLeague Two · England | 3–2 | League Two · England |
| 2008-03-11 | GrimsbyvBarnetLeague Two · England | 4–1 | League Two · England |
| 2008-03-07 | GrimsbyvMilton Keynes DonsLeague Two · England | 0–1 | League Two · England |
| 2008-03-01 | MorecambevGrimsbyLeague Two · England | 0–4 | League Two · England |
| 2008-02-23 | WrexhamvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2008-02-16 | GrimsbyvDag and RedLeague Two · England | 1–4 | League Two · England |
| 2008-02-12 | MacclesfieldvGrimsbyLeague Two · England | 1–2 | League Two · England |
| 2008-02-09 | GrimsbyvChesterfieldLeague Two · England | 4–2 | League Two · England |
| 2008-02-02 | Notts CountyvGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2008-01-29 | GrimsbyvBuryLeague Two · England | 1–0 | League Two · England |
| 2008-01-26 | GrimsbyvShrewsburyLeague Two · England | 1–1 | League Two · England |
| 2008-01-19 | Dag and RedvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2008-01-12 | GrimsbyvWrexhamLeague Two · England | 1–0 | League Two · England |
| 2008-01-05 | ChesterfieldvGrimsbyLeague Two · England | 1–2 | League Two · England |
| 2008-01-01 | ChestervGrimsbyLeague Two · England | 0–2 | League Two · England |