| 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 |
| 2014-03-03 | ChesterfieldvPortsmouthLeague Two · England | 0–0 | League Two · England |
| 2014-02-25 | CheltenhamvChesterfieldLeague Two · England | 1–4 | League Two · England |
| 2014-02-22 | WycombevChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2014-02-15 | ChesterfieldvTorquayLeague Two · England | 3–1 | League Two · England |
| 2014-02-08 | ScunthorpevChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2014-02-01 | ChesterfieldvBristol RvsLeague Two · England | 3–1 | League Two · England |
| 2014-01-28 | YorkvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2014-01-25 | NorthamptonvChesterfieldLeague Two · England | 1–3 | League Two · England |
| 2014-01-21 | ChesterfieldvRochdaleLeague Two · England | 2–2 | League Two · England |
| 2014-01-18 | SouthendvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2014-01-11 | ChesterfieldvBuryLeague Two · England | 4–0 | League Two · England |