| 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 |
| 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 |
| 2014-05-03 | ChesterfieldvFleetwood TownLeague Two · England | 2–1 | League Two · England |
| 2014-04-27 | BurtonvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2014-04-21 | Dag and RedvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2014-04-18 | ChesterfieldvExeterLeague Two · England | 1–1 | League Two · England |
| 2014-04-12 | HartlepoolvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2014-04-05 | ChesterfieldvNewport CountyLeague Two · England | 1–1 | League Two · England |
| 2014-03-25 | ChesterfieldvMorecambeLeague Two · England | 1–0 | League Two · England |
| 2014-03-22 | MansfieldvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2014-03-18 | PlymouthvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2014-03-15 | ChesterfieldvOxfordLeague Two · England | 3–0 | League Two · England |
| 2014-03-11 | AFC WimbledonvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2014-03-08 | AccringtonvChesterfieldLeague Two · England | 3–1 | League Two · England |