| 2008-12-28 | GillinghamvWycombeLeague Two · England | 1–1 | League Two · England |
| 2008-12-26 | Dag and RedvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2008-12-20 | GillinghamvBrentfordLeague Two · England | 1–1 | League Two · England |
| 2008-12-13 | BarnetvGillinghamLeague Two · England | 2–2 | League Two · England |
| 2008-12-06 | GillinghamvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2008-11-25 | GillinghamvRochdaleLeague Two · England | 1–1 | League Two · England |
| 2008-11-22 | BuryvGillinghamLeague Two · England | 4–0 | League Two · England |
| 2008-11-15 | GillinghamvRotherhamLeague Two · England | 4–0 | League Two · England |
| 2008-11-01 | MacclesfieldvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2008-10-28 | LincolnvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2008-10-25 | GillinghamvChesterLeague Two · England | 2–0 | League Two · England |
| 2008-10-21 | GillinghamvNotts CountyLeague Two · England | 2–2 | League Two · England |
| 2008-10-18 | BradfordvGillinghamLeague Two · England | 2–2 | League Two · England |
| 2008-10-11 | GillinghamvMorecambeLeague Two · England | 5–0 | League Two · England |
| 2008-10-04 | ExetervGillinghamLeague Two · England | 3–0 | League Two · England |
| 2008-09-27 | GillinghamvPort ValeLeague Two · England | 1–0 | League Two · England |
| 2008-09-20 | AldershotvGillinghamLeague Two · England | 2–1 | League Two · England |
| 2008-09-13 | ShrewsburyvGillinghamLeague Two · England | 7–0 | League Two · England |
| 2008-09-06 | GillinghamvGrimsbyLeague Two · England | 3–0 | League Two · England |
| 2008-08-30 | GillinghamvAccringtonLeague Two · England | 1–0 | League Two · England |
| 2008-08-23 | DarlingtonvGillinghamLeague Two · England | 1–2 | League Two · England |
| 2008-08-16 | GillinghamvLutonLeague Two · England | 0–1 | League Two · England |
| 2008-08-09 | BournemouthvGillinghamLeague Two · England | 1–1 | League Two · England |