| 2017-04-30 | Sheffield UnitedvChesterfieldLeague One · England | 3–2 | League One · England |
| 2017-04-22 | ChesterfieldvCharltonLeague One · England | 1–2 | League One · England |
| 2017-04-17 | ScunthorpevChesterfieldLeague One · England | 3–1 | League One · England |
| 2017-04-14 | ChesterfieldvSouthendLeague One · England | 0–4 | League One · England |
| 2017-04-08 | ChesterfieldvPort ValeLeague One · England | 1–0 | League One · England |
| 2017-04-01 | BoltonvChesterfieldLeague One · England | 0–0 | League One · England |
| 2017-03-25 | ChesterfieldvRochdaleLeague One · England | 1–3 | League One · England |
| 2017-03-18 | Bristol RvsvChesterfieldLeague One · England | 2–1 | League One · England |
| 2017-03-14 | ChesterfieldvPeterboroLeague One · England | 3–3 | League One · England |
| 2017-03-11 | ChesterfieldvShrewsburyLeague One · England | 1–1 | League One · England |
| 2017-03-07 | WalsallvChesterfieldLeague One · England | 1–0 | League One · England |
| 2017-03-04 | SwindonvChesterfieldLeague One · England | 0–1 | League One · England |
| 2017-02-25 | ChesterfieldvOxfordLeague One · England | 0–4 | League One · England |
| 2017-02-21 | MillwallvChesterfieldLeague One · England | 0–0 | League One · England |
| 2017-02-18 | ChesterfieldvBuryLeague One · England | 1–2 | League One · England |
| 2017-02-14 | GillinghamvChesterfieldLeague One · England | 1–1 | League One · England |
| 2017-02-11 | NorthamptonvChesterfieldLeague One · England | 3–1 | League One · England |
| 2017-02-04 | ChesterfieldvOldhamLeague One · England | 0–1 | League One · England |
| 2017-01-21 | ChesterfieldvAFC WimbledonLeague One · England | 0–0 | League One · England |
| 2017-01-14 | ChesterfieldvCoventryLeague One · England | 1–0 | League One · England |
| 2017-01-07 | BradfordvChesterfieldLeague One · England | 2–0 | League One · England |
| 2017-01-02 | ChesterfieldvMilton Keynes DonsLeague One · England | 0–0 | League One · England |
| 2016-12-30 | Port ValevChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-12-26 | RochdalevChesterfieldLeague One · England | 3–0 | League One · England |
| 2016-12-17 | ChesterfieldvBoltonLeague One · England | 1–0 | League One · England |
| 2016-12-10 | PeterborovChesterfieldLeague One · England | 5–2 | League One · England |
| 2016-11-26 | ChesterfieldvBristol RvsLeague One · England | 3–2 | League One · England |
| 2016-11-22 | Milton Keynes DonsvChesterfieldLeague One · England | 2–3 | League One · England |
| 2016-11-19 | Fleetwood TownvChesterfieldLeague One · England | 2–1 | League One · England |
| 2016-11-13 | ChesterfieldvSheffield UnitedLeague One · England | 1–4 | League One · England |
| 2016-11-01 | CoventryvChesterfieldLeague One · England | 2–0 | League One · England |
| 2016-10-29 | CharltonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-10-22 | ChesterfieldvScunthorpeLeague One · England | 0–3 | League One · England |
| 2016-10-18 | ChesterfieldvFleetwood TownLeague One · England | 0–1 | League One · England |
| 2016-10-15 | SouthendvChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-10-01 | ChesterfieldvBradfordLeague One · England | 0–1 | League One · England |
| 2016-09-27 | ChesterfieldvGillinghamLeague One · England | 3–3 | League One · England |
| 2016-09-24 | BuryvChesterfieldLeague One · England | 2–1 | League One · England |
| 2016-09-17 | ChesterfieldvNorthamptonLeague One · England | 3–1 | League One · England |
| 2016-09-10 | OldhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 2016-09-03 | AFC WimbledonvChesterfieldLeague One · England | 2–1 | League One · England |
| 2016-08-27 | ChesterfieldvMillwallLeague One · England | 1–3 | League One · England |
| 2016-08-20 | ShrewsburyvChesterfieldLeague One · England | 2–1 | League One · England |
| 2016-08-16 | ChesterfieldvWalsallLeague One · England | 2–0 | League One · England |
| 2016-08-13 | ChesterfieldvSwindonLeague One · England | 3–1 | League One · England |
| 2016-08-06 | OxfordvChesterfieldLeague One · England | 1–1 | League One · England |
| 2016-05-08 | BradfordvChesterfieldLeague One · England | 2–0 | League One · England |
| 2016-04-30 | ChesterfieldvBuryLeague One · England | 3–0 | League One · England |
| 2016-04-23 | SwindonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2016-04-19 | ChesterfieldvDoncasterLeague One · England | 1–1 | League One · England |