| 2005-12-31 | GillinghamvMilton Keynes DonsLeague One · England | 3–0 | League One · England |
| 2005-12-26 | GillinghamvBristol CityLeague One · England | 1–1 | League One · England |
| 2005-12-17 | BournemouthvGillinghamLeague One · England | 2–1 | League One · England |
| 2005-12-10 | GillinghamvPort ValeLeague One · England | 3–0 | League One · England |
| 2005-12-06 | GillinghamvDoncasterLeague One · England | 1–0 | League One · England |
| 2005-11-26 | ColchestervGillinghamLeague One · England | 5–0 | League One · England |
| 2005-11-19 | GillinghamvHartlepoolLeague One · England | 1–0 | League One · England |
| 2005-11-12 | WalsallvGillinghamLeague One · England | 2–0 | League One · England |
| 2005-11-01 | HartlepoolvGillinghamLeague One · England | 3–1 | League One · England |
| 2005-10-29 | GillinghamvBlackpoolLeague One · England | 2–1 | League One · England |
| 2005-10-22 | BradfordvGillinghamLeague One · England | 1–0 | League One · England |
| 2005-10-15 | GillinghamvYeovilLeague One · England | 0–0 | League One · England |
| 2005-10-01 | GillinghamvSouthendLeague One · England | 1–2 | League One · England |
| 2005-09-27 | GillinghamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-09-24 | TranmerevGillinghamLeague One · England | 2–2 | League One · England |
| 2005-09-17 | GillinghamvOldhamLeague One · England | 0–1 | League One · England |
| 2005-09-13 | GillinghamvBarnsleyLeague One · England | 0–3 | League One · England |
| 2005-09-10 | RotherhamvGillinghamLeague One · England | 3–0 | League One · England |
| 2005-08-29 | BrentfordvGillinghamLeague One · England | 1–1 | League One · England |
| 2005-08-27 | GillinghamvNott'm ForestLeague One · England | 1–3 | League One · England |
| 2005-08-20 | GillinghamvBournemouthLeague One · England | 1–0 | League One · England |
| 2005-08-13 | ScunthorpevGillinghamLeague One · England | 1–1 | League One · England |
| 2005-08-09 | Port ValevGillinghamLeague One · England | 0–0 | League One · England |
| 2005-08-06 | GillinghamvColchesterLeague One · England | 2–1 | League One · England |