| 2024-12-29 | BradfordvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2024-12-26 | Fleetwood TownvChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2024-12-21 | ChesterfieldvAFC WimbledonLeague Two · England | 1–0 | League Two · England |
| 2024-12-14 | CarlislevChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2024-12-07 | ChesterfieldvTranmereLeague Two · England | 3–0 | League Two · England |
| 2024-12-03 | Milton Keynes DonsvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2024-11-23 | ChesterfieldvBarrowLeague Two · England | 1–0 | League Two · England |
| 2024-11-16 | HarrogatevChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2024-11-09 | ChesterfieldvAccringtonLeague Two · England | 0–3 | League Two · England |
| 2024-10-26 | MorecambevChesterfieldLeague Two · England | 2–5 | League Two · England |
| 2024-10-22 | ChesterfieldvColchesterLeague Two · England | 1–1 | League Two · England |
| 2024-10-18 | Newport CountyvChesterfieldLeague Two · England | 0–3 | League Two · England |
| 2024-10-12 | ChesterfieldvNotts CountyLeague Two · England | 2–2 | League Two · England |
| 2024-10-05 | ChesterfieldvWalsallLeague Two · England | 2–2 | League Two · England |
| 2024-10-01 | BromleyvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2024-09-28 | DoncastervChesterfieldLeague Two · England | 0–3 | League Two · England |
| 2024-09-21 | ChesterfieldvCheltenhamLeague Two · England | 1–1 | League Two · England |
| 2024-09-14 | Port ValevChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2024-09-07 | ChesterfieldvGrimsbyLeague Two · England | 2–1 | League Two · England |
| 2024-08-31 | GillinghamvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2024-08-24 | ChesterfieldvSalfordLeague Two · England | 1–1 | League Two · England |
| 2024-08-17 | CrewevChesterfieldLeague Two · England | 0–5 | League Two · England |
| 2024-08-09 | ChesterfieldvSwindonLeague Two · England | 1–1 | League Two · England |