| 2024-03-12 | AFC WimbledonvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2024-03-09 | GillinghamvTranmereLeague Two · England | 1–1 | League Two · England |
| 2024-03-05 | BarrowvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2024-03-02 | SalfordvGillinghamLeague Two · England | 0–2 | League Two · England |
| 2024-02-24 | GillinghamvWrexhamLeague Two · England | 1–0 | League Two · England |
| 2024-02-20 | GillinghamvStockportLeague Two · England | 0–0 | League Two · England |
| 2024-02-17 | Newport CountyvGillinghamLeague Two · England | 1–0 | League Two · England |
| 2024-02-13 | GillinghamvSwindonLeague Two · England | 2–2 | League Two · England |
| 2024-02-09 | Notts CountyvGillinghamLeague Two · England | 1–3 | League Two · England |
| 2024-02-03 | GillinghamvWalsallLeague Two · England | 1–1 | League Two · England |
| 2024-01-27 | Milton Keynes DonsvGillinghamLeague Two · England | 2–1 | League Two · England |
| 2024-01-20 | GillinghamvForest GreenLeague Two · England | 1–1 | League Two · England |
| 2024-01-13 | AccringtonvGillinghamLeague Two · England | 1–2 | League Two · England |
| 2024-01-01 | ColchestervGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-12-29 | GillinghamvSuttonLeague Two · England | 1–0 | League Two · England |
| 2023-12-26 | GillinghamvCrawley TownLeague Two · England | 0–2 | League Two · England |
| 2023-12-22 | Forest GreenvGillinghamLeague Two · England | 0–0 | League Two · England |
| 2023-12-16 | GillinghamvBradfordLeague Two · England | 0–2 | League Two · England |
| 2023-11-28 | GillinghamvAFC WimbledonLeague Two · England | 1–0 | League Two · England |
| 2023-11-25 | TranmerevGillinghamLeague Two · England | 3–1 | League Two · England |
| 2023-11-18 | GillinghamvSalfordLeague Two · England | 3–1 | League Two · England |
| 2023-11-11 | WrexhamvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2023-10-28 | GillinghamvNewport CountyLeague Two · England | 0–2 | League Two · England |
| 2023-10-24 | SwindonvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-10-21 | GillinghamvNotts CountyLeague Two · England | 1–2 | League Two · England |
| 2023-10-14 | WalsallvGillinghamLeague Two · England | 4–1 | League Two · England |
| 2023-10-07 | GillinghamvMilton Keynes DonsLeague Two · England | 2–1 | League Two · England |
| 2023-10-03 | CrewevGillinghamLeague Two · England | 2–0 | League Two · England |
| 2023-09-30 | GillinghamvMansfieldLeague Two · England | 1–1 | League Two · England |
| 2023-09-23 | DoncastervGillinghamLeague Two · England | 2–1 | League Two · England |
| 2023-09-16 | GillinghamvMorecambeLeague Two · England | 2–1 | League Two · England |
| 2023-09-09 | GillinghamvHarrogateLeague Two · England | 1–0 | League Two · England |
| 2023-09-02 | GrimsbyvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2023-08-26 | GillinghamvColchesterLeague Two · England | 0–3 | League Two · England |
| 2023-08-19 | Crawley TownvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-08-15 | SuttonvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-08-12 | GillinghamvAccringtonLeague Two · England | 1–0 | League Two · England |
| 2023-08-05 | StockportvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-05-08 | SalfordvGillinghamLeague Two · England | 0–1 | League Two · England |
| 2023-04-29 | GillinghamvNewport CountyLeague Two · England | 1–2 | League Two · England |
| 2023-04-22 | BradfordvGillinghamLeague Two · England | 2–2 | League Two · England |
| 2023-04-18 | GillinghamvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 2023-04-15 | GillinghamvStockportLeague Two · England | 1–1 | League Two · England |
| 2023-04-10 | NorthamptonvGillinghamLeague Two · England | 2–1 | League Two · England |
| 2023-04-07 | GillinghamvDoncasterLeague Two · England | 1–0 | League Two · England |
| 2023-04-01 | BarrowvGillinghamLeague Two · England | 2–1 | League Two · England |
| 2023-03-25 | GillinghamvCarlisleLeague Two · England | 1–0 | League Two · England |
| 2023-03-21 | GillinghamvCreweLeague Two · England | 2–1 | League Two · England |
| 2023-03-18 | WalsallvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2023-03-11 | GillinghamvTranmereLeague Two · England | 2–0 | League Two · England |