| 1996-11-19 | PeterborovGillinghamLeague One · England | 0–1 | League One · England |
| 1996-11-09 | GillinghamvWrexhamLeague One · England | 1–2 | League One · England |
| 1996-11-02 | Bristol RvsvGillinghamLeague One · England | 0–0 | League One · England |
| 1996-10-29 | PlymouthvGillinghamLeague One · England | 2–0 | League One · England |
| 1996-10-26 | GillinghamvPrestonLeague One · England | 1–1 | League One · England |
| 1996-10-19 | GillinghamvMillwallLeague One · England | 2–3 | League One · England |
| 1996-10-15 | ShrewsburyvGillinghamLeague One · England | 1–2 | League One · England |
| 1996-10-12 | BlackpoolvGillinghamLeague One · England | 2–0 | League One · England |
| 1996-10-05 | GillinghamvBournemouthLeague One · England | 1–1 | League One · England |
| 1996-10-01 | GillinghamvNotts CountyLeague One · England | 1–0 | League One · England |
| 1996-09-28 | StockportvGillinghamLeague One · England | 2–1 | League One · England |
| 1996-09-21 | GillinghamvRotherhamLeague One · England | 3–1 | League One · England |
| 1996-09-14 | WalsallvGillinghamLeague One · England | 1–0 | League One · England |
| 1996-09-10 | LutonvGillinghamLeague One · England | 2–1 | League One · England |
| 1996-09-07 | GillinghamvBurnleyLeague One · England | 1–0 | League One · England |
| 1996-08-31 | GillinghamvChesterfieldLeague One · England | 0–1 | League One · England |
| 1996-08-27 | BrentfordvGillinghamLeague One · England | 2–0 | League One · England |
| 1996-08-24 | WycombevGillinghamLeague One · England | 1–1 | League One · England |
| 1996-08-17 | GillinghamvBristol CityLeague One · England | 3–2 | League One · England |
| 1996-05-04 | GillinghamvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1996-04-27 | FulhamvGillinghamLeague Two · England | 0–0 | League Two · England |
| 1996-04-20 | NorthamptonvGillinghamLeague Two · England | 1–1 | League Two · England |
| 1996-04-16 | ColchestervGillinghamLeague Two · England | 1–1 | League Two · England |
| 1996-04-13 | GillinghamvExeterLeague Two · England | 1–0 | League Two · England |
| 1996-04-08 | DoncastervGillinghamLeague Two · England | 0–1 | League Two · England |
| 1996-04-06 | GillinghamvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1996-04-02 | GillinghamvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1996-03-30 | RochdalevGillinghamLeague Two · England | 2–0 | League Two · England |
| 1996-03-23 | GillinghamvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-03-16 | MansfieldvGillinghamLeague Two · England | 0–1 | League Two · England |
| 1996-03-12 | TorquayvGillinghamLeague Two · England | 0–0 | League Two · England |
| 1996-03-09 | GillinghamvPrestonLeague Two · England | 1–1 | League Two · England |
| 1996-03-02 | PlymouthvGillinghamLeague Two · England | 1–0 | League Two · England |
| 1996-02-27 | GillinghamvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1996-02-24 | CardiffvGillinghamLeague Two · England | 2–0 | League Two · England |
| 1996-02-17 | GillinghamvHerefordLeague Two · England | 1–1 | League Two · England |
| 1996-02-13 | GillinghamvBarnetLeague Two · England | 1–0 | League Two · England |
| 1996-02-10 | GillinghamvTorquayLeague Two · England | 2–0 | League Two · England |
| 1996-02-03 | CambridgevGillinghamLeague Two · England | 0–0 | League Two · England |
| 1996-01-30 | GillinghamvMansfieldLeague Two · England | 2–0 | League Two · England |
| 1996-01-20 | WiganvGillinghamLeague Two · England | 2–1 | League Two · England |
| 1996-01-13 | GillinghamvLincolnLeague Two · England | 2–0 | League Two · England |
| 1996-01-09 | GillinghamvChesterLeague Two · England | 3–1 | League Two · England |
| 1996-01-01 | Leyton OrientvGillinghamLeague Two · England | 0–1 | League Two · England |
| 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 |