| 1993-12-28 | ScunthorpevChesterfieldLeague Two · England | 2–2 | League Two · England |
| 1993-12-18 | ChesterfieldvGillinghamLeague Two · England | 3–2 | League Two · England |
| 1993-11-27 | NorthamptonvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 1993-11-20 | ChesterfieldvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1993-11-06 | BuryvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 1993-11-02 | ChesterfieldvWiganLeague Two · England | 1–0 | League Two · England |
| 1993-10-30 | ChesterfieldvCreweLeague Two · England | 2–0 | League Two · England |
| 1993-10-23 | LincolnvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 1993-10-16 | ChesterfieldvTorquayLeague Two · England | 3–1 | League Two · England |
| 1993-10-09 | PrestonvChesterfieldLeague Two · England | 4–1 | League Two · England |
| 1993-10-02 | ChesterfieldvWycombeLeague Two · England | 2–3 | League Two · England |
| 1993-09-25 | RochdalevChesterfieldLeague Two · England | 5–1 | League Two · England |
| 1993-09-18 | ChesterfieldvWalsallLeague Two · England | 0–1 | League Two · England |
| 1993-09-11 | CarlislevChesterfieldLeague Two · England | 3–0 | League Two · England |
| 1993-09-04 | ChesterfieldvDarlingtonLeague Two · England | 1–1 | League Two · England |
| 1993-08-31 | ChesterfieldvMansfieldLeague Two · England | 0–2 | League Two · England |
| 1993-08-28 | ChestervChesterfieldLeague Two · England | 3–1 | League Two · England |
| 1993-08-21 | ChesterfieldvHerefordLeague Two · England | 3–1 | League Two · England |
| 1993-08-14 | GillinghamvChesterfieldLeague Two · England | 0–2 | League Two · England |