| 2025-12-29 | ChesterfieldvCambridgeLeague Two · England | 0–1 | League Two · England |
| 2025-12-26 | ChesterfieldvNotts CountyLeague Two · England | 2–0 | League Two · England |
| 2025-12-20 | ShrewsburyvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2025-12-13 | ChesterfieldvBarnetLeague Two · England | 3–1 | League Two · England |
| 2025-12-09 | CambridgevChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2025-11-29 | ChesterfieldvSwindonLeague Two · England | 1–2 | League Two · England |
| 2025-11-22 | CrewevChesterfieldLeague Two · England | 3–3 | League Two · England |
| 2025-11-15 | GrimsbyvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2025-11-08 | ChesterfieldvAccringtonLeague Two · England | 3–3 | League Two · England |
| 2025-10-25 | TranmerevChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2025-10-18 | ChesterfieldvFleetwood TownLeague Two · England | 1–1 | League Two · England |
| 2025-10-11 | ChesterfieldvSalfordLeague Two · England | 2–0 | League Two · England |
| 2025-10-04 | ColchestervChesterfieldLeague Two · England | 6–2 | League Two · England |
| 2025-09-27 | ChesterfieldvNewport CountyLeague Two · England | 4–1 | League Two · England |
| 2025-09-20 | BromleyvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2025-09-13 | ChesterfieldvMilton Keynes DonsLeague Two · England | 1–1 | League Two · England |
| 2025-09-06 | WalsallvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2025-08-30 | ChesterfieldvCrawley TownLeague Two · England | 2–2 | League Two · England |
| 2025-08-23 | HarrogatevChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2025-08-19 | GillinghamvChesterfieldLeague Two · England | 4–1 | League Two · England |
| 2025-08-16 | ChesterfieldvBristol RvsLeague Two · England | 3–1 | League Two · England |
| 2025-08-09 | CheltenhamvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2025-08-02 | ChesterfieldvBarrowLeague Two · England | 1–0 | League Two · England |
| 2025-05-03 | AccringtonvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2025-04-26 | ChesterfieldvMorecambeLeague Two · England | 4–1 | League Two · England |
| 2025-04-21 | ChesterfieldvBradfordLeague Two · England | 3–3 | League Two · England |
| 2025-04-18 | AFC WimbledonvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 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 |