| 2017-12-30 | ChesterfieldvColchesterLeague Two · England | 0–0 | League Two · England |
| 2017-12-26 | ChesterfieldvCreweLeague Two · England | 0–2 | League Two · England |
| 2017-12-23 | StevenagevChesterfieldLeague Two · England | 5–1 | League Two · England |
| 2017-12-16 | WycombevChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2017-12-09 | ChesterfieldvBarnetLeague Two · England | 2–1 | League Two · England |
| 2017-11-25 | MansfieldvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2017-11-21 | ChesterfieldvForest GreenLeague Two · England | 3–2 | League Two · England |
| 2017-11-18 | ChesterfieldvExeterLeague Two · England | 1–0 | League Two · England |
| 2017-11-11 | SwindonvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2017-10-28 | ChesterfieldvCarlisleLeague Two · England | 2–2 | League Two · England |
| 2017-10-21 | CambridgevChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2017-10-17 | Crawley TownvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2017-10-14 | ChesterfieldvMorecambeLeague Two · England | 0–2 | League Two · England |
| 2017-10-07 | LincolnvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2017-09-30 | ChesterfieldvCheltenhamLeague Two · England | 0–2 | League Two · England |
| 2017-09-26 | ChesterfieldvYeovilLeague Two · England | 2–3 | League Two · England |
| 2017-09-23 | LutonvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2017-09-16 | ChesterfieldvAccringtonLeague Two · England | 1–2 | League Two · England |
| 2017-09-12 | ColchestervChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2017-09-09 | CrewevChesterfieldLeague Two · England | 5–1 | League Two · England |
| 2017-09-02 | ChesterfieldvCoventryLeague Two · England | 0–0 | League Two · England |
| 2017-08-26 | Newport CountyvChesterfieldLeague Two · England | 4–1 | League Two · England |
| 2017-08-19 | ChesterfieldvPort ValeLeague Two · England | 2–0 | League Two · England |
| 2017-08-12 | Notts CountyvChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2017-08-05 | ChesterfieldvGrimsbyLeague Two · England | 1–3 | League Two · England |