| 2025-04-12 | ChesterfieldvFleetwood TownLeague Two · England | 3–0 | League Two · England |
| 2025-04-08 | ChesterfieldvGillinghamLeague Two · England | 1–1 | League Two · England |
| 2025-04-05 | TranmerevChesterfieldLeague Two · England | 4–0 | League Two · England |
| 2025-04-01 | ChesterfieldvCarlisleLeague Two · England | 2–1 | League Two · England |
| 2025-03-29 | BarrowvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2025-03-22 | ChesterfieldvHarrogateLeague Two · England | 0–0 | League Two · England |
| 2025-03-15 | Notts CountyvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2025-03-11 | SalfordvChesterfieldLeague Two · England | 0–4 | League Two · England |
| 2025-03-08 | ChesterfieldvNewport CountyLeague Two · England | 2–1 | League Two · England |
| 2025-03-04 | ColchestervChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2025-03-01 | ChesterfieldvCreweLeague Two · England | 1–3 | League Two · England |
| 2025-02-22 | SwindonvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2025-02-15 | WalsallvChesterfieldLeague Two · England | 3–1 | League Two · England |
| 2025-02-06 | ChesterfieldvDoncasterLeague Two · England | 5–2 | League Two · England |
| 2025-02-01 | CheltenhamvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2025-01-28 | ChesterfieldvBromleyLeague Two · England | 3–0 | League Two · England |
| 2025-01-25 | ChesterfieldvPort ValeLeague Two · England | 1–1 | League Two · England |
| 2025-01-18 | GrimsbyvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2025-01-01 | ChesterfieldvMilton Keynes DonsLeague Two · England | 1–2 | League Two · England |
| 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 |
| 2018-05-05 | BarnetvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2018-05-01 | ChesterfieldvNewport CountyLeague Two · England | 1–0 | League Two · England |
| 2018-04-28 | ChesterfieldvWycombeLeague Two · England | 1–2 | League Two · England |
| 2018-04-21 | Forest GreenvChesterfieldLeague Two · England | 4–1 | League Two · England |
| 2018-04-17 | ExetervChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2018-04-14 | ChesterfieldvMansfieldLeague Two · England | 0–1 | League Two · England |
| 2018-04-10 | MorecambevChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2018-04-07 | GrimsbyvChesterfieldLeague Two · England | 1–0 | League Two · England |