| 2006-01-02 | ChesterfieldvBarnsleyLeague One · England | 0–0 | League One · England |
| 2005-12-31 | Nott'm ForestvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-12-28 | ChesterfieldvSwindonLeague One · England | 1–1 | League One · England |
| 2005-12-26 | ScunthorpevChesterfieldLeague One · England | 2–2 | League One · England |
| 2005-12-17 | ChesterfieldvOldhamLeague One · England | 1–1 | League One · England |
| 2005-12-10 | BrentfordvChesterfieldLeague One · England | 1–1 | League One · England |
| 2005-12-06 | SouthendvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-11-26 | ChesterfieldvBlackpoolLeague One · England | 1–1 | League One · England |
| 2005-11-19 | Bristol CityvChesterfieldLeague One · England | 2–4 | League One · England |
| 2005-11-12 | ChesterfieldvPort ValeLeague One · England | 2–0 | League One · England |
| 2005-10-29 | SwanseavChesterfieldLeague One · England | 5–1 | League One · England |
| 2005-10-26 | ChesterfieldvBristol CityLeague One · England | 3–0 | League One · England |
| 2005-10-22 | ChesterfieldvHuddersfieldLeague One · England | 4–3 | League One · England |
| 2005-10-15 | Milton Keynes DonsvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-10-01 | ColchestervChesterfieldLeague One · England | 1–2 | League One · England |
| 2005-09-27 | GillinghamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-09-24 | ChesterfieldvHartlepoolLeague One · England | 3–1 | League One · England |
| 2005-09-17 | WalsallvChesterfieldLeague One · England | 2–3 | League One · England |
| 2005-09-10 | ChesterfieldvBournemouthLeague One · England | 3–0 | League One · England |
| 2005-09-02 | BradfordvChesterfieldLeague One · England | 2–0 | League One · England |
| 2005-08-29 | YeovilvChesterfieldLeague One · England | 1–3 | League One · England |
| 2005-08-27 | ChesterfieldvTranmereLeague One · England | 0–2 | League One · England |
| 2005-08-20 | OldhamvChesterfieldLeague One · England | 4–1 | League One · England |
| 2005-08-13 | ChesterfieldvRotherhamLeague One · England | 0–1 | League One · England |
| 2005-08-10 | ChesterfieldvBrentfordLeague One · England | 1–3 | League One · England |
| 2005-08-06 | BlackpoolvChesterfieldLeague One · England | 1–3 | League One · England |
| 2005-05-07 | SwindonvChesterfieldLeague One · England | 1–1 | League One · England |
| 2005-04-30 | ChesterfieldvOldhamLeague One · England | 1–0 | League One · England |
| 2005-04-23 | BlackpoolvChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-04-16 | ChesterfieldvBournemouthLeague One · England | 2–3 | League One · England |
| 2005-04-09 | Port ValevChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-04-02 | ChesterfieldvBradfordLeague One · England | 0–0 | League One · England |
| 2005-03-28 | ColchestervChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-03-26 | ChesterfieldvTranmereLeague One · England | 2–2 | League One · England |
| 2005-03-19 | BrentfordvChesterfieldLeague One · England | 2–2 | League One · England |
| 2005-03-12 | ChesterfieldvHuddersfieldLeague One · England | 2–1 | League One · England |
| 2005-03-05 | TorquayvChesterfieldLeague One · England | 2–2 | League One · England |
| 2005-02-26 | ChesterfieldvPeterboroLeague One · England | 1–3 | League One · England |
| 2005-02-22 | StockportvChesterfieldLeague One · England | 1–2 | League One · England |
| 2005-02-19 | ChesterfieldvSheffield WedsLeague One · England | 1–3 | League One · England |
| 2005-02-12 | DoncastervChesterfieldLeague One · England | 0–1 | League One · England |
| 2005-02-05 | ChesterfieldvHartlepoolLeague One · England | 0–1 | League One · England |
| 2005-02-01 | ChesterfieldvHullLeague One · England | 1–1 | League One · England |
| 2005-01-28 | Bristol CityvChesterfieldLeague One · England | 2–3 | League One · England |
| 2005-01-22 | ChesterfieldvWrexhamLeague One · England | 2–4 | League One · England |
| 2005-01-15 | WalsallvChesterfieldLeague One · England | 3–0 | League One · England |
| 2005-01-03 | ChesterfieldvBarnsleyLeague One · England | 2–2 | League One · England |
| 2005-01-01 | Milton Keynes DonsvChesterfieldLeague One · England | 1–1 | League One · England |
| 2004-12-28 | WrexhamvChesterfieldLeague One · England | 3–1 | League One · England |
| 2004-12-26 | ChesterfieldvLutonLeague One · England | 0–1 | League One · England |