| 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 |
| 2018-03-30 | Port ValevChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2018-03-25 | ChesterfieldvNotts CountyLeague Two · England | 3–1 | League Two · England |
| 2018-03-17 | CheltenhamvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2018-03-10 | ChesterfieldvLincolnLeague Two · England | 1–3 | League Two · England |
| 2018-02-24 | ChesterfieldvSwindonLeague Two · England | 2–1 | League Two · England |
| 2018-02-17 | CarlislevChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2018-02-13 | ChesterfieldvCambridgeLeague Two · England | 2–3 | League Two · England |
| 2018-02-03 | ChesterfieldvCrawley TownLeague Two · England | 1–2 | League Two · England |
| 2018-01-27 | ChesterfieldvStevenageLeague Two · England | 0–1 | League Two · England |
| 2018-01-20 | YeovilvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2018-01-13 | ChesterfieldvLutonLeague Two · England | 2–0 | League Two · England |
| 2018-01-06 | AccringtonvChesterfieldLeague Two · England | 4–0 | League Two · England |
| 2018-01-01 | CoventryvChesterfieldLeague Two · England | 1–0 | League Two · England |