| 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 |