| 2016-04-16 | ChesterfieldvSheffield UnitedLeague One · England | 0–3 | League One · England |
| 2016-04-09 | BarnsleyvChesterfieldLeague One · England | 1–2 | League One · England |
| 2016-04-02 | ChesterfieldvPort ValeLeague One · England | 4–2 | League One · England |
| 2016-03-28 | OldhamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-03-26 | ChesterfieldvFleetwood TownLeague One · England | 0–0 | League One · England |
| 2016-03-19 | ScunthorpevChesterfieldLeague One · England | 1–1 | League One · England |
| 2016-03-12 | ChesterfieldvWalsallLeague One · England | 1–4 | League One · England |
| 2016-03-05 | SouthendvChesterfieldLeague One · England | 0–1 | League One · England |
| 2016-03-01 | ChesterfieldvBlackpoolLeague One · England | 1–1 | League One · England |
| 2016-02-27 | GillinghamvChesterfieldLeague One · England | 1–2 | League One · England |
| 2016-02-20 | ChesterfieldvCreweLeague One · England | 3–1 | League One · England |
| 2016-02-16 | ColchestervChesterfieldLeague One · England | 1–1 | League One · England |
| 2016-02-12 | BurtonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-02-06 | ChesterfieldvPeterboroLeague One · England | 0–1 | League One · England |
| 2016-01-23 | ChesterfieldvMillwallLeague One · England | 1–2 | League One · England |
| 2016-01-16 | WiganvChesterfieldLeague One · England | 3–1 | League One · England |
| 2016-01-09 | RochdalevChesterfieldLeague One · England | 2–3 | League One · England |
| 2016-01-02 | ChesterfieldvShrewsburyLeague One · England | 7–1 | League One · England |
| 2015-12-28 | ChesterfieldvCoventryLeague One · England | 1–1 | League One · England |
| 2015-12-26 | PeterborovChesterfieldLeague One · England | 2–0 | League One · England |
| 2015-12-19 | ChesterfieldvBradfordLeague One · England | 0–1 | League One · England |
| 2015-12-12 | BuryvChesterfieldLeague One · England | 1–0 | League One · England |
| 2015-11-28 | ChesterfieldvSwindonLeague One · England | 0–4 | League One · England |
| 2015-11-24 | DoncastervChesterfieldLeague One · England | 3–0 | League One · England |
| 2015-11-21 | Port ValevChesterfieldLeague One · England | 3–2 | League One · England |
| 2015-11-14 | ChesterfieldvOldhamLeague One · England | 1–2 | League One · England |
| 2015-10-31 | Fleetwood TownvChesterfieldLeague One · England | 0–1 | League One · England |
| 2015-10-24 | ChesterfieldvScunthorpeLeague One · England | 0–3 | League One · England |
| 2015-10-20 | ChesterfieldvSouthendLeague One · England | 3–0 | League One · England |
| 2015-10-17 | WalsallvChesterfieldLeague One · England | 1–2 | League One · England |
| 2015-10-10 | ChesterfieldvGillinghamLeague One · England | 1–3 | League One · England |
| 2015-10-03 | CrewevChesterfieldLeague One · England | 1–2 | League One · England |
| 2015-09-29 | BlackpoolvChesterfieldLeague One · England | 2–0 | League One · England |
| 2015-09-26 | ChesterfieldvBurtonLeague One · England | 1–2 | League One · England |
| 2015-09-19 | CoventryvChesterfieldLeague One · England | 1–0 | League One · England |
| 2015-09-12 | ChesterfieldvColchesterLeague One · England | 3–3 | League One · England |
| 2015-09-05 | ChesterfieldvWiganLeague One · England | 2–3 | League One · England |
| 2015-08-29 | MillwallvChesterfieldLeague One · England | 0–2 | League One · England |
| 2015-08-22 | ChesterfieldvRochdaleLeague One · England | 0–0 | League One · England |
| 2015-08-18 | ShrewsburyvChesterfieldLeague One · England | 1–2 | League One · England |
| 2015-08-15 | Sheffield UnitedvChesterfieldLeague One · England | 2–0 | League One · England |
| 2015-08-08 | ChesterfieldvBarnsleyLeague One · England | 3–1 | League One · England |
| 2015-05-03 | Sheffield UnitedvChesterfieldLeague One · England | 1–1 | League One · England |
| 2015-04-25 | ChesterfieldvBristol CityLeague One · England | 0–2 | League One · England |
| 2015-04-18 | OldhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 2015-04-14 | ChesterfieldvColchesterLeague One · England | 6–0 | League One · England |
| 2015-04-11 | BarnsleyvChesterfieldLeague One · England | 1–1 | League One · England |
| 2015-04-06 | ChesterfieldvCreweLeague One · England | 1–0 | League One · England |
| 2015-04-03 | YeovilvChesterfieldLeague One · England | 2–3 | League One · England |
| 2015-03-31 | BradfordvChesterfieldLeague One · England | 0–1 | League One · England |