| 2014-12-28 | GillinghamvBristol CityLeague One · England | 1–3 | League One · England |
| 2014-12-26 | ColchestervGillinghamLeague One · England | 1–2 | League One · England |
| 2014-12-20 | GillinghamvChesterfieldLeague One · England | 2–3 | League One · England |
| 2014-12-13 | DoncastervGillinghamLeague One · England | 1–2 | League One · England |
| 2014-11-29 | GillinghamvPort ValeLeague One · England | 2–2 | League One · England |
| 2014-11-22 | BradfordvGillinghamLeague One · England | 1–1 | League One · England |
| 2014-11-15 | GillinghamvLeyton OrientLeague One · England | 3–2 | League One · England |
| 2014-11-01 | Fleetwood TownvGillinghamLeague One · England | 1–0 | League One · England |
| 2014-10-25 | GillinghamvCrawley TownLeague One · England | 1–1 | League One · England |
| 2014-10-21 | GillinghamvPrestonLeague One · England | 0–1 | League One · England |
| 2014-10-18 | RochdalevGillinghamLeague One · England | 1–1 | League One · England |
| 2014-10-11 | GillinghamvScunthorpeLeague One · England | 0–3 | League One · England |
| 2014-10-04 | Notts CountyvGillinghamLeague One · England | 1–0 | League One · England |
| 2014-09-27 | Sheffield UnitedvGillinghamLeague One · England | 2–1 | League One · England |
| 2014-09-20 | GillinghamvWalsallLeague One · England | 0–0 | League One · England |
| 2014-09-16 | GillinghamvPeterboroLeague One · England | 2–1 | League One · England |
| 2014-09-13 | OldhamvGillinghamLeague One · England | 0–0 | League One · England |
| 2014-09-05 | CoventryvGillinghamLeague One · England | 1–0 | League One · England |
| 2014-08-30 | GillinghamvCreweLeague One · England | 2–0 | League One · England |
| 2014-08-23 | BarnsleyvGillinghamLeague One · England | 4–1 | League One · England |
| 2014-08-19 | GillinghamvSwindonLeague One · England | 2–2 | League One · England |
| 2014-08-16 | GillinghamvYeovilLeague One · England | 2–0 | League One · England |
| 2014-08-09 | Milton Keynes DonsvGillinghamLeague One · England | 4–2 | League One · England |
| 2014-05-03 | GillinghamvShrewsburyLeague One · England | 1–1 | League One · England |
| 2014-04-26 | PrestonvGillinghamLeague One · England | 3–1 | League One · England |
| 2014-04-21 | WalsallvGillinghamLeague One · England | 1–1 | League One · England |
| 2014-04-18 | GillinghamvTranmereLeague One · England | 2–0 | League One · England |
| 2014-04-12 | Leyton OrientvGillinghamLeague One · England | 5–1 | League One · England |
| 2014-04-08 | PeterborovGillinghamLeague One · England | 2–0 | League One · England |
| 2014-04-05 | GillinghamvRotherhamLeague One · England | 3–4 | League One · England |
| 2014-03-25 | Milton Keynes DonsvGillinghamLeague One · England | 0–1 | League One · England |
| 2014-03-22 | GillinghamvCreweLeague One · England | 1–3 | League One · England |
| 2014-03-15 | BradfordvGillinghamLeague One · England | 1–1 | League One · England |
| 2014-03-11 | GillinghamvCoventryLeague One · England | 4–2 | League One · England |
| 2014-03-08 | GillinghamvCrawley TownLeague One · England | 1–0 | League One · England |
| 2014-03-01 | Bristol CityvGillinghamLeague One · England | 2–1 | League One · England |
| 2014-02-22 | OldhamvGillinghamLeague One · England | 1–0 | League One · England |
| 2014-02-19 | GillinghamvSheffield UnitedLeague One · England | 0–1 | League One · England |
| 2014-02-08 | CarlislevGillinghamLeague One · England | 1–2 | League One · England |
| 2014-02-04 | StevenagevGillinghamLeague One · England | 3–1 | League One · England |
| 2014-02-01 | GillinghamvPort ValeLeague One · England | 3–2 | League One · England |
| 2014-01-24 | BrentfordvGillinghamLeague One · England | 2–1 | League One · England |
| 2014-01-18 | GillinghamvSwindonLeague One · England | 2–0 | League One · England |
| 2014-01-11 | ColchestervGillinghamLeague One · England | 3–0 | League One · England |
| 2014-01-03 | GillinghamvWolvesLeague One · England | 1–0 | League One · England |