| 1995-12-26 | GillinghamvPlymouthLeague Two · England | 1–0 | League Two · England |
| 1995-12-23 | PrestonvGillinghamLeague Two · England | 0–0 | League Two · England |
| 1995-12-16 | BuryvGillinghamLeague Two · England | 1–0 | League Two · England |
| 1995-11-25 | GillinghamvFulhamLeague Two · England | 1–0 | League Two · England |
| 1995-11-18 | ScarboroughvGillinghamLeague Two · England | 0–2 | League Two · England |
| 1995-11-04 | GillinghamvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 1995-10-31 | ExetervGillinghamLeague Two · England | 0–0 | League Two · England |
| 1995-10-28 | HartlepoolvGillinghamLeague Two · England | 1–1 | League Two · England |
| 1995-10-21 | GillinghamvDoncasterLeague Two · England | 4–0 | League Two · England |
| 1995-10-14 | DarlingtonvGillinghamLeague Two · England | 1–0 | League Two · England |
| 1995-10-07 | GillinghamvRochdaleLeague Two · England | 1–0 | League Two · England |
| 1995-09-30 | GillinghamvBuryLeague Two · England | 3–0 | League Two · England |
| 1995-09-23 | ChestervGillinghamLeague Two · England | 1–1 | League Two · England |
| 1995-09-16 | GillinghamvCardiffLeague Two · England | 1–0 | League Two · England |
| 1995-09-12 | HerefordvGillinghamLeague Two · England | 0–0 | League Two · England |
| 1995-09-09 | ScunthorpevGillinghamLeague Two · England | 1–1 | League Two · England |
| 1995-09-02 | GillinghamvColchesterLeague Two · England | 0–1 | League Two · England |
| 1995-08-29 | BarnetvGillinghamLeague Two · England | 0–2 | League Two · England |
| 1995-08-26 | GillinghamvCambridgeLeague Two · England | 3–0 | League Two · England |
| 1995-08-19 | LincolnvGillinghamLeague Two · England | 0–3 | League Two · England |
| 1995-08-12 | GillinghamvWiganLeague Two · England | 2–1 | League Two · England |
| 1995-05-06 | TorquayvGillinghamLeague Two · England | 3–1 | League Two · England |
| 1995-04-29 | GillinghamvHerefordLeague Two · England | 0–0 | League Two · England |
| 1995-04-22 | GillinghamvDoncasterLeague Two · England | 4–2 | League Two · England |
| 1995-04-17 | FulhamvGillinghamLeague Two · England | 1–0 | League Two · England |
| 1995-04-15 | GillinghamvBarnetLeague Two · England | 2–1 | League Two · England |
| 1995-04-11 | GillinghamvColchesterLeague Two · England | 1–3 | League Two · England |
| 1995-04-08 | CarlislevGillinghamLeague Two · England | 2–0 | League Two · England |
| 1995-04-04 | GillinghamvBuryLeague Two · England | 1–1 | League Two · England |
| 1995-04-01 | PrestonvGillinghamLeague Two · England | 1–1 | League Two · England |
| 1995-03-25 | GillinghamvExeterLeague Two · England | 3–0 | League Two · England |
| 1995-03-18 | GillinghamvScunthorpeLeague Two · England | 2–2 | League Two · England |
| 1995-03-11 | ScarboroughvGillinghamLeague Two · England | 0–0 | League Two · England |
| 1995-03-04 | GillinghamvWalsallLeague Two · England | 1–3 | League Two · England |
| 1995-02-25 | MansfieldvGillinghamLeague Two · England | 4–0 | League Two · England |
| 1995-02-21 | DarlingtonvGillinghamLeague Two · England | 2–0 | League Two · England |
| 1995-02-18 | GillinghamvNorthamptonLeague Two · England | 3–1 | League Two · England |
| 1995-02-11 | ChesterfieldvGillinghamLeague Two · England | 2–0 | League Two · England |
| 1995-02-04 | GillinghamvLincolnLeague Two · England | 0–0 | League Two · England |
| 1995-02-01 | DoncastervGillinghamLeague Two · England | 1–2 | League Two · England |
| 1995-01-14 | NorthamptonvGillinghamLeague Two · England | 2–0 | League Two · England |