| 2016-12-30 | MillwallvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-12-26 | PeterborovGillinghamLeague One · England | 1–1 | League One · England |
| 2016-12-17 | GillinghamvMilton Keynes DonsLeague One · England | 1–0 | League One · England |
| 2016-12-12 | BoltonvGillinghamLeague One · England | 4–0 | League One · England |
| 2016-11-26 | GillinghamvRochdaleLeague One · England | 3–0 | League One · England |
| 2016-11-22 | OxfordvGillinghamLeague One · England | 1–0 | League One · England |
| 2016-11-19 | WalsallvGillinghamLeague One · England | 1–2 | League One · England |
| 2016-11-12 | GillinghamvNorthamptonLeague One · England | 2–1 | League One · England |
| 2016-10-29 | Fleetwood TownvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-10-22 | GillinghamvCharltonLeague One · England | 1–1 | League One · England |
| 2016-10-18 | GillinghamvWalsallLeague One · England | 1–1 | League One · England |
| 2016-10-15 | Bristol RvsvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-10-08 | GillinghamvOldhamLeague One · England | 1–2 | League One · England |
| 2016-10-01 | AFC WimbledonvGillinghamLeague One · England | 2–0 | League One · England |
| 2016-09-27 | ChesterfieldvGillinghamLeague One · England | 3–3 | League One · England |
| 2016-09-24 | GillinghamvCoventryLeague One · England | 2–1 | League One · England |
| 2016-09-17 | Port ValevGillinghamLeague One · England | 2–1 | League One · England |
| 2016-09-10 | GillinghamvBradfordLeague One · England | 1–1 | League One · England |
| 2016-09-04 | GillinghamvSheffield UnitedLeague One · England | 1–2 | League One · England |
| 2016-08-27 | ShrewsburyvGillinghamLeague One · England | 2–3 | League One · England |
| 2016-08-20 | ScunthorpevGillinghamLeague One · England | 5–0 | League One · England |
| 2016-08-16 | GillinghamvSwindonLeague One · England | 1–1 | League One · England |
| 2016-08-13 | GillinghamvBuryLeague One · England | 2–1 | League One · England |
| 2016-08-06 | SouthendvGillinghamLeague One · England | 1–3 | League One · England |
| 2016-05-08 | GillinghamvMillwallLeague One · England | 1–2 | League One · England |
| 2016-04-30 | BurtonvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-04-23 | GillinghamvShrewsburyLeague One · England | 2–3 | League One · England |
| 2016-04-19 | RochdalevGillinghamLeague One · England | 1–1 | League One · England |
| 2016-04-16 | GillinghamvPort ValeLeague One · England | 0–2 | League One · England |
| 2016-04-12 | GillinghamvWalsallLeague One · England | 1–2 | League One · England |
| 2016-04-09 | Sheffield UnitedvGillinghamLeague One · England | 0–0 | League One · England |
| 2016-04-02 | GillinghamvCoventryLeague One · England | 0–0 | League One · England |
| 2016-03-28 | BuryvGillinghamLeague One · England | 0–1 | League One · England |
| 2016-03-19 | SouthendvGillinghamLeague One · England | 1–1 | League One · England |
| 2016-03-12 | GillinghamvCreweLeague One · England | 3–0 | League One · England |
| 2016-03-05 | ScunthorpevGillinghamLeague One · England | 0–0 | League One · England |
| 2016-03-01 | Fleetwood TownvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-02-27 | GillinghamvChesterfieldLeague One · England | 1–2 | League One · England |
| 2016-02-20 | OldhamvGillinghamLeague One · England | 2–1 | League One · England |
| 2016-02-13 | GillinghamvBarnsleyLeague One · England | 2–1 | League One · England |
| 2016-02-06 | GillinghamvSwindonLeague One · England | 0–0 | League One · England |
| 2016-01-30 | BlackpoolvGillinghamLeague One · England | 1–0 | League One · England |
| 2016-01-23 | GillinghamvPeterboroLeague One · England | 2–1 | League One · England |
| 2016-01-16 | DoncastervGillinghamLeague One · England | 2–2 | League One · England |
| 2016-01-07 | WiganvGillinghamLeague One · England | 3–2 | League One · England |
| 2016-01-02 | GillinghamvBradfordLeague One · England | 3–0 | League One · England |