| 1999-12-26 | LutonvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-12-10 | BrentfordvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-12-07 | ChesterfieldvBristol CityLeague One · England | 0–2 | League One · England |
| 1999-12-03 | ColchestervChesterfieldLeague One · England | 1–0 | League One · England |
| 1999-11-27 | ChesterfieldvOxfordLeague One · England | 0–0 | League One · England |
| 1999-11-20 | ChesterfieldvBristol RvsLeague One · England | 0–1 | League One · England |
| 1999-11-12 | CardiffvChesterfieldLeague One · England | 2–1 | League One · England |
| 1999-11-06 | ChesterfieldvOldhamLeague One · England | 0–1 | League One · England |
| 1999-11-02 | WiganvChesterfieldLeague One · England | 3–0 | League One · England |
| 1999-10-23 | ChesterfieldvScunthorpeLeague One · England | 1–1 | League One · England |
| 1999-10-19 | Notts CountyvChesterfieldLeague One · England | 1–0 | League One · England |
| 1999-10-16 | WrexhamvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-10-09 | ChesterfieldvBlackpoolLeague One · England | 0–0 | League One · England |
| 1999-10-02 | ChesterfieldvBournemouthLeague One · England | 0–1 | League One · England |
| 1999-09-25 | ScunthorpevChesterfieldLeague One · England | 0–0 | League One · England |
| 1999-09-18 | ReadingvChesterfieldLeague One · England | 1–0 | League One · England |
| 1999-09-11 | ChesterfieldvStokeLeague One · England | 0–2 | League One · England |
| 1999-09-04 | PrestonvChesterfieldLeague One · England | 0–2 | League One · England |
| 1999-08-28 | MillwallvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-08-21 | ChesterfieldvCambridgeLeague One · England | 4–2 | League One · England |
| 1999-08-14 | BurnleyvChesterfieldLeague One · England | 2–1 | League One · England |
| 1999-08-07 | ChesterfieldvColchesterLeague One · England | 0–1 | League One · England |
| 1999-05-08 | WiganvChesterfieldLeague One · England | 3–1 | League One · England |
| 1999-05-03 | ChesterfieldvNorthamptonLeague One · England | 0–0 | League One · England |
| 1999-04-27 | LutonvChesterfieldLeague One · England | 1–0 | League One · England |
| 1999-04-24 | BournemouthvChesterfieldLeague One · England | 0–0 | League One · England |
| 1999-04-20 | ChesterfieldvBristol RvsLeague One · England | 0–0 | League One · England |
| 1999-04-17 | ChesterfieldvFulhamLeague One · England | 1–0 | League One · England |
| 1999-04-13 | MacclesfieldvChesterfieldLeague One · England | 2–0 | League One · England |
| 1999-04-10 | Notts CountyvChesterfieldLeague One · England | 2–0 | League One · England |
| 1999-04-05 | ChesterfieldvStokeLeague One · England | 1–1 | League One · England |
| 1999-04-03 | YorkvChesterfieldLeague One · England | 1–2 | League One · England |
| 1999-03-27 | ChesterfieldvBlackpoolLeague One · England | 1–2 | League One · England |
| 1999-03-20 | ChesterfieldvLutonLeague One · England | 3–1 | League One · England |
| 1999-03-13 | LincolnvChesterfieldLeague One · England | 2–0 | League One · England |
| 1999-03-06 | WrexhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 1999-03-02 | ChesterfieldvMillwallLeague One · England | 2–1 | League One · England |
| 1999-02-27 | ChesterfieldvMan CityLeague One · England | 1–1 | League One · England |
| 1999-02-20 | WalsallvChesterfieldLeague One · England | 1–1 | League One · England |
| 1999-02-06 | GillinghamvChesterfieldLeague One · England | 3–1 | League One · England |
| 1999-01-30 | ChesterfieldvWycombeLeague One · England | 2–0 | League One · England |
| 1999-01-23 | ChesterfieldvPrestonLeague One · England | 0–1 | League One · England |
| 1999-01-16 | BurnleyvChesterfieldLeague One · England | 1–2 | League One · England |
| 1999-01-09 | ChesterfieldvColchesterLeague One · England | 3–1 | League One · England |
| 1999-01-02 | ReadingvChesterfieldLeague One · England | 1–2 | League One · England |