| 2009-05-02 | RochdalevGillinghamLeague Two · England | 0–1 | League Two · England |
| 2009-04-25 | GillinghamvBuryLeague Two · England | 0–0 | League Two · England |
| 2009-04-18 | ChesterfieldvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2009-04-13 | GillinghamvDag and RedLeague Two · England | 2–1 | League Two · England |
| 2009-04-11 | WycombevGillinghamLeague Two · England | 1–0 | League Two · England |
| 2009-04-04 | GillinghamvBarnetLeague Two · England | 0–2 | League Two · England |
| 2009-03-28 | BrentfordvGillinghamLeague Two · England | 1–1 | League Two · England |
| 2009-03-21 | GrimsbyvGillinghamLeague Two · England | 3–0 | League Two · England |
| 2009-03-17 | Notts CountyvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2009-03-14 | GillinghamvShrewsburyLeague Two · England | 2–2 | League Two · England |
| 2009-03-10 | GillinghamvDarlingtonLeague Two · England | 1–0 | League Two · England |
| 2009-03-07 | AccringtonvGillinghamLeague Two · England | 0–2 | League Two · England |
| 2009-03-03 | LutonvGillinghamLeague Two · England | 0–0 | League Two · England |
| 2009-02-28 | GillinghamvBournemouthLeague Two · England | 1–0 | League Two · England |
| 2009-02-21 | GillinghamvMacclesfieldLeague Two · England | 3–1 | League Two · England |
| 2009-02-17 | GillinghamvAldershotLeague Two · England | 4–4 | League Two · England |
| 2009-02-14 | RotherhamvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2009-02-07 | GillinghamvBradfordLeague Two · England | 0–2 | League Two · England |
| 2009-01-31 | ChestervGillinghamLeague Two · England | 0–1 | League Two · England |
| 2009-01-27 | GillinghamvLincolnLeague Two · England | 1–2 | League Two · England |
| 2009-01-24 | GillinghamvExeterLeague Two · England | 1–0 | League Two · England |
| 2009-01-20 | Port ValevGillinghamLeague Two · England | 1–3 | League Two · England |
| 2009-01-17 | MorecambevGillinghamLeague Two · England | 0–1 | League Two · England |