| 1996-04-13 | ChesterfieldvBristol CityLeague One · England | 1–1 | League One · England |
| 1996-04-09 | ShrewsburyvChesterfieldLeague One · England | 0–0 | League One · England |
| 1996-04-06 | ChesterfieldvStockportLeague One · England | 1–2 | League One · England |
| 1996-04-02 | ChesterfieldvBlackpoolLeague One · England | 1–0 | League One · England |
| 1996-03-30 | CrewevChesterfieldLeague One · England | 3–0 | League One · England |
| 1996-03-26 | Bristol RvsvChesterfieldLeague One · England | 1–0 | League One · England |
| 1996-03-23 | ChesterfieldvBristol RvsLeague One · England | 2–1 | League One · England |
| 1996-03-19 | ChesterfieldvWrexhamLeague One · England | 1–1 | League One · England |
| 1996-03-16 | WalsallvChesterfieldLeague One · England | 3–0 | League One · England |
| 1996-03-12 | HullvChesterfieldLeague One · England | 0–0 | League One · England |
| 1996-03-09 | ChesterfieldvBrightonLeague One · England | 1–0 | League One · England |
| 1996-03-05 | WrexhamvChesterfieldLeague One · England | 3–0 | League One · England |
| 1996-03-02 | PeterborovChesterfieldLeague One · England | 0–1 | League One · England |
| 1996-02-24 | RotherhamvChesterfieldLeague One · England | 0–1 | League One · England |
| 1996-02-17 | ChesterfieldvWycombeLeague One · England | 3–1 | League One · England |
| 1996-02-03 | ChesterfieldvSwanseaLeague One · England | 3–2 | League One · England |
| 1996-01-20 | ChesterfieldvOxfordLeague One · England | 1–0 | League One · England |
| 1996-01-13 | CarlislevChesterfieldLeague One · England | 1–1 | League One · England |
| 1995-12-26 | ChesterfieldvPeterboroLeague One · England | 1–1 | League One · England |
| 1995-12-22 | BrightonvChesterfieldLeague One · England | 0–2 | League One · England |
| 1995-12-16 | ChesterfieldvBrentfordLeague One · England | 2–2 | League One · England |
| 1995-12-09 | BurnleyvChesterfieldLeague One · England | 2–2 | League One · England |
| 1995-11-25 | ChesterfieldvBournemouthLeague One · England | 3–0 | League One · England |
| 1995-11-18 | Notts CountyvChesterfieldLeague One · England | 4–1 | League One · England |
| 1995-11-04 | ChesterfieldvBradfordLeague One · England | 2–1 | League One · England |
| 1995-10-31 | Bristol CityvChesterfieldLeague One · England | 2–1 | League One · England |
| 1995-10-28 | StockportvChesterfieldLeague One · England | 0–1 | League One · England |
| 1995-10-21 | ChesterfieldvShrewsburyLeague One · England | 1–0 | League One · England |
| 1995-10-14 | BlackpoolvChesterfieldLeague One · England | 0–0 | League One · England |
| 1995-10-07 | ChesterfieldvCreweLeague One · England | 1–2 | League One · England |
| 1995-09-30 | BrentfordvChesterfieldLeague One · England | 1–2 | League One · England |
| 1995-09-23 | ChesterfieldvBurnleyLeague One · England | 4–2 | League One · England |
| 1995-09-16 | ChesterfieldvRotherhamLeague One · England | 3–0 | League One · England |
| 1995-09-12 | WycombevChesterfieldLeague One · England | 1–0 | League One · England |
| 1995-09-09 | SwindonvChesterfieldLeague One · England | 1–1 | League One · England |
| 1995-09-02 | ChesterfieldvHullLeague One · England | 0–0 | League One · England |
| 1995-08-29 | ChesterfieldvYorkLeague One · England | 2–1 | League One · England |
| 1995-08-26 | SwanseavChesterfieldLeague One · England | 3–2 | League One · England |
| 1995-08-19 | ChesterfieldvCarlisleLeague One · England | 3–0 | League One · England |
| 1995-08-12 | OxfordvChesterfieldLeague One · England | 1–0 | League One · England |