| 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 |
| 1995-05-06 | ChesterfieldvColchesterLeague Two · England | 2–2 | League Two · England |
| 1995-05-02 | ChesterfieldvCarlisleLeague Two · England | 1–2 | League Two · England |
| 1995-04-29 | DarlingtonvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 1995-04-17 | DoncastervChesterfieldLeague Two · England | 1–3 | League Two · England |
| 1995-04-15 | ChesterfieldvNorthamptonLeague Two · England | 3–0 | League Two · England |
| 1995-04-08 | LincolnvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 1995-04-04 | CarlislevChesterfieldLeague Two · England | 1–1 | League Two · England |
| 1995-04-01 | ExetervChesterfieldLeague Two · England | 1–2 | League Two · England |
| 1995-03-25 | ChesterfieldvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1995-03-18 | ChesterfieldvWiganLeague Two · England | 0–0 | League Two · England |
| 1995-03-11 | WalsallvChesterfieldLeague Two · England | 1–3 | League Two · England |
| 1995-03-04 | ChesterfieldvBuryLeague Two · England | 0–0 | League Two · England |
| 1995-02-25 | TorquayvChesterfieldLeague Two · England | 3–3 | League Two · England |
| 1995-02-18 | ScunthorpevChesterfieldLeague Two · England | 0–1 | League Two · England |
| 1995-02-14 | ChesterfieldvBarnetLeague Two · England | 2–0 | League Two · England |
| 1995-02-11 | ChesterfieldvGillinghamLeague Two · England | 2–0 | League Two · England |
| 1995-02-04 | PrestonvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 1995-01-24 | HerefordvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 1995-01-14 | ChesterfieldvScunthorpeLeague Two · England | 3–1 | League Two · England |
| 1995-01-08 | FulhamvChesterfieldLeague Two · England | 1–1 | League Two · England |