| 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 |
| 2008-05-03 | LeedsvGillinghamLeague One · England | 2–1 | League One · England |
| 2008-04-26 | GillinghamvSwindonLeague One · England | 1–1 | League One · England |
| 2008-04-19 | Bristol RvsvGillinghamLeague One · England | 1–1 | League One · England |
| 2008-04-12 | GillinghamvSwanseaLeague One · England | 1–2 | League One · England |
| 2008-04-05 | MillwallvGillinghamLeague One · England | 1–1 | League One · England |
| 2008-04-01 | GillinghamvLutonLeague One · England | 2–1 | League One · England |
| 2008-03-29 | GillinghamvCarlisleLeague One · England | 0–0 | League One · England |
| 2008-03-24 | Port ValevGillinghamLeague One · England | 2–1 | League One · England |
| 2008-03-22 | GillinghamvBournemouthLeague One · England | 2–1 | League One · England |
| 2008-03-15 | GillinghamvCreweLeague One · England | 0–3 | League One · England |
| 2008-03-11 | DoncastervGillinghamLeague One · England | 2–1 | League One · England |
| 2008-03-08 | HartlepoolvGillinghamLeague One · England | 4–0 | League One · England |
| 2008-03-04 | BrightonvGillinghamLeague One · England | 4–2 | League One · England |
| 2008-03-01 | GillinghamvYeovilLeague One · England | 0–0 | League One · England |
| 2008-02-23 | GillinghamvHuddersfieldLeague One · England | 1–0 | League One · England |
| 2008-02-16 | NorthamptonvGillinghamLeague One · England | 4–0 | League One · England |
| 2008-02-09 | OldhamvGillinghamLeague One · England | 2–1 | League One · England |
| 2008-02-02 | GillinghamvCheltenhamLeague One · England | 0–0 | League One · England |
| 2008-01-29 | TranmerevGillinghamLeague One · England | 2–0 | League One · England |
| 2008-01-26 | WalsallvGillinghamLeague One · England | 2–1 | League One · England |
| 2008-01-22 | GillinghamvOldhamLeague One · England | 0–0 | League One · England |
| 2008-01-19 | GillinghamvNorthamptonLeague One · England | 0–1 | League One · England |
| 2008-01-12 | HuddersfieldvGillinghamLeague One · England | 1–3 | League One · England |
| 2008-01-01 | Leyton OrientvGillinghamLeague One · England | 0–0 | League One · England |