| 1997-11-29 | ChesterfieldvSouthendLeague One · England | 1–0 | League One · England |
| 1997-11-22 | MillwallvChesterfieldLeague One · England | 1–1 | League One · England |
| 1997-11-18 | CarlislevChesterfieldLeague One · England | 0–2 | League One · England |
| 1997-11-08 | ChesterfieldvGrimsbyLeague One · England | 1–0 | League One · England |
| 1997-11-04 | ChesterfieldvGillinghamLeague One · England | 1–1 | League One · England |
| 1997-11-01 | FulhamvChesterfieldLeague One · England | 1–1 | League One · England |
| 1997-10-25 | ChesterfieldvWycombeLeague One · England | 1–0 | League One · England |
| 1997-10-21 | BlackpoolvChesterfieldLeague One · England | 2–1 | League One · England |
| 1997-10-18 | OldhamvChesterfieldLeague One · England | 2–0 | League One · England |
| 1997-10-11 | ChesterfieldvWiganLeague One · England | 2–3 | League One · England |
| 1997-10-04 | ChesterfieldvBournemouthLeague One · England | 1–1 | League One · England |
| 1997-09-27 | WrexhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 1997-09-20 | ChesterfieldvBristol RvsLeague One · England | 0–0 | League One · England |
| 1997-09-13 | WatfordvChesterfieldLeague One · England | 2–1 | League One · England |
| 1997-09-07 | ChesterfieldvBurnleyLeague One · England | 1–0 | League One · England |
| 1997-09-02 | YorkvChesterfieldLeague One · England | 0–1 | League One · England |
| 1997-08-30 | PlymouthvChesterfieldLeague One · England | 1–1 | League One · England |
| 1997-08-23 | ChesterfieldvPrestonLeague One · England | 3–2 | League One · England |
| 1997-08-16 | BrentfordvChesterfieldLeague One · England | 0–0 | League One · England |
| 1997-08-09 | ChesterfieldvWalsallLeague One · England | 3–1 | League One · England |
| 1997-05-03 | ChesterfieldvNotts CountyLeague One · England | 1–0 | League One · England |
| 1997-04-30 | Bristol CityvChesterfieldLeague One · England | 2–0 | League One · England |
| 1997-04-28 | ChesterfieldvStockportLeague One · England | 0–1 | League One · England |
| 1997-04-26 | CrewevChesterfieldLeague One · England | 1–2 | League One · England |
| 1997-04-24 | WatfordvChesterfieldLeague One · England | 0–2 | League One · England |
| 1997-04-19 | ChesterfieldvMillwallLeague One · England | 1–0 | League One · England |
| 1997-04-15 | BrentfordvChesterfieldLeague One · England | 1–0 | League One · England |
| 1997-04-08 | ChesterfieldvWatfordLeague One · England | 0–0 | League One · England |
| 1997-04-05 | ChesterfieldvGillinghamLeague One · England | 2–2 | League One · England |
| 1997-04-01 | WalsallvChesterfieldLeague One · England | 1–1 | League One · England |
| 1997-03-29 | ChesterfieldvBlackpoolLeague One · England | 0–0 | League One · England |
| 1997-03-22 | BuryvChesterfieldLeague One · England | 1–0 | League One · England |
| 1997-03-15 | ChesterfieldvWycombeLeague One · England | 4–2 | League One · England |
| 1997-03-11 | BournemouthvChesterfieldLeague One · England | 3–0 | League One · England |
| 1997-03-04 | ChesterfieldvLutonLeague One · England | 1–1 | League One · England |
| 1997-03-01 | PeterborovChesterfieldLeague One · England | 1–1 | League One · England |
| 1997-02-22 | ChesterfieldvPlymouthLeague One · England | 1–2 | League One · England |
| 1997-02-18 | ChesterfieldvRotherhamLeague One · England | 1–1 | League One · England |
| 1997-02-08 | ChesterfieldvWrexhamLeague One · England | 0–0 | League One · England |
| 1997-02-01 | PrestonvChesterfieldLeague One · England | 0–1 | League One · England |
| 1997-01-28 | BurnleyvChesterfieldLeague One · England | 0–0 | League One · England |
| 1997-01-18 | ShrewsburyvChesterfieldLeague One · England | 2–0 | League One · England |
| 1997-01-11 | ChesterfieldvBristol RvsLeague One · England | 1–0 | League One · England |
| 1996-12-21 | ChesterfieldvBournemouthLeague One · England | 1–1 | League One · England |
| 1996-12-14 | WycombevChesterfieldLeague One · England | 1–0 | League One · England |
| 1996-12-03 | ChesterfieldvPeterboroLeague One · England | 2–1 | League One · England |
| 1996-11-30 | YorkvChesterfieldLeague One · England | 0–0 | League One · England |
| 1996-11-19 | PlymouthvChesterfieldLeague One · England | 0–3 | League One · England |
| 1996-11-09 | ChesterfieldvPrestonLeague One · England | 2–1 | League One · England |
| 1996-11-02 | WrexhamvChesterfieldLeague One · England | 3–2 | League One · England |