| 2009-12-28 | GrimsbyvPort ValeLeague Two · England | 1–2 | League Two · England |
| 2009-12-18 | GrimsbyvMorecambeLeague Two · England | 1–1 | League Two · England |
| 2009-12-12 | ShrewsburyvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2009-12-05 | GrimsbyvDag and RedLeague Two · England | 1–1 | League Two · England |
| 2009-11-28 | MacclesfieldvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2009-11-24 | GrimsbyvBradfordLeague Two · England | 0–3 | League Two · England |
| 2009-11-21 | LincolnvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2009-11-14 | NorthamptonvGrimsbyLeague Two · England | 0–0 | League Two · England |
| 2009-10-30 | GrimsbyvAccringtonLeague Two · England | 2–2 | League Two · England |
| 2009-10-24 | BournemouthvGrimsbyLeague Two · England | 3–1 | League Two · England |
| 2009-10-17 | GrimsbyvRochdaleLeague Two · England | 0–2 | League Two · England |
| 2009-10-10 | GrimsbyvBurtonLeague Two · England | 1–2 | League Two · England |
| 2009-10-03 | BarnetvGrimsbyLeague Two · England | 3–0 | League Two · England |
| 2009-09-30 | ChesterfieldvGrimsbyLeague Two · England | 3–2 | League Two · England |
| 2009-09-26 | GrimsbyvDarlingtonLeague Two · England | 1–1 | League Two · England |
| 2009-09-19 | TorquayvGrimsbyLeague Two · England | 0–2 | League Two · England |
| 2009-09-12 | GrimsbyvHerefordLeague Two · England | 1–0 | League Two · England |
| 2009-09-05 | Port ValevGrimsbyLeague Two · England | 4–0 | League Two · England |
| 2009-08-29 | GrimsbyvAldershotLeague Two · England | 1–2 | League Two · England |
| 2009-08-22 | BuryvGrimsbyLeague Two · England | 0–1 | League Two · England |
| 2009-08-18 | GrimsbyvRotherhamLeague Two · England | 1–2 | League Two · England |
| 2009-08-15 | GrimsbyvCreweLeague Two · England | 0–4 | League Two · England |
| 2009-08-08 | CheltenhamvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2009-05-02 | GrimsbyvMacclesfieldLeague Two · England | 0–0 | League Two · England |
| 2009-04-25 | BournemouthvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2009-04-18 | GrimsbyvPort ValeLeague Two · England | 3–0 | League Two · England |
| 2009-04-13 | Notts CountyvGrimsbyLeague Two · England | 0–2 | League Two · England |
| 2009-04-11 | GrimsbyvAccringtonLeague Two · England | 0–1 | League Two · England |
| 2009-04-04 | ShrewsburyvGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2009-03-28 | GrimsbyvAldershotLeague Two · England | 1–0 | League Two · England |
| 2009-03-21 | GrimsbyvGillinghamLeague Two · England | 3–0 | League Two · England |
| 2009-03-17 | LutonvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2009-03-14 | ChestervGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2009-03-11 | ChesterfieldvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2009-03-07 | GrimsbyvLincolnLeague Two · England | 5–1 | League Two · England |
| 2009-03-03 | GrimsbyvBrentfordLeague Two · England | 0–1 | League Two · England |
| 2009-02-28 | RochdalevGrimsbyLeague Two · England | 2–0 | League Two · England |
| 2009-02-24 | GrimsbyvMorecambeLeague Two · England | 2–3 | League Two · England |
| 2009-02-21 | DarlingtonvGrimsbyLeague Two · England | 1–0 | League Two · England |
| 2009-02-14 | GrimsbyvBuryLeague Two · England | 1–2 | League Two · England |
| 2009-02-10 | BarnetvGrimsbyLeague Two · England | 3–3 | League Two · England |
| 2009-02-07 | GrimsbyvExeterLeague Two · England | 2–2 | League Two · England |
| 2009-01-31 | BradfordvGrimsbyLeague Two · England | 2–0 | League Two · England |
| 2009-01-27 | GrimsbyvDag and RedLeague Two · England | 1–1 | League Two · England |
| 2009-01-24 | GrimsbyvRotherhamLeague Two · England | 3–0 | League Two · England |
| 2009-01-17 | WycombevGrimsbyLeague Two · England | 0–1 | League Two · England |