| 2014-12-28 | CoventryvChesterfieldLeague One · England | 0–0 | League One · England |
| 2014-12-26 | ChesterfieldvPeterboroLeague One · England | 3–2 | League One · England |
| 2014-12-20 | GillinghamvChesterfieldLeague One · England | 2–3 | League One · England |
| 2014-12-13 | ChesterfieldvBradfordLeague One · England | 0–1 | League One · England |
| 2014-11-29 | Crawley TownvChesterfieldLeague One · England | 1–1 | League One · England |
| 2014-11-22 | ChesterfieldvBarnsleyLeague One · England | 2–1 | League One · England |
| 2014-11-15 | CrewevChesterfieldLeague One · England | 0–0 | League One · England |
| 2014-11-01 | ChesterfieldvYeovilLeague One · England | 0–0 | League One · England |
| 2014-10-28 | ChesterfieldvSwindonLeague One · England | 0–3 | League One · England |
| 2014-10-25 | WalsallvChesterfieldLeague One · England | 1–0 | League One · England |
| 2014-10-21 | ColchestervChesterfieldLeague One · England | 2–1 | League One · England |
| 2014-10-18 | ChesterfieldvOldhamLeague One · England | 1–1 | League One · England |
| 2014-10-11 | Bristol CityvChesterfieldLeague One · England | 3–2 | League One · England |
| 2014-10-04 | ChesterfieldvSheffield UnitedLeague One · England | 3–2 | League One · England |
| 2014-09-27 | ChesterfieldvNotts CountyLeague One · England | 1–1 | League One · England |
| 2014-09-20 | DoncastervChesterfieldLeague One · England | 3–2 | League One · England |
| 2014-09-16 | PrestonvChesterfieldLeague One · England | 3–3 | League One · England |
| 2014-09-13 | ChesterfieldvScunthorpeLeague One · England | 4–1 | League One · England |
| 2014-08-30 | Port ValevChesterfieldLeague One · England | 1–2 | League One · England |
| 2014-08-23 | Fleetwood TownvChesterfieldLeague One · England | 0–0 | League One · England |
| 2014-08-19 | ChesterfieldvMilton Keynes DonsLeague One · England | 0–1 | League One · England |
| 2014-08-16 | ChesterfieldvRochdaleLeague One · England | 2–1 | League One · England |
| 2014-08-09 | Leyton OrientvChesterfieldLeague One · England | 1–2 | League One · 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 |
| 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 |