| 2003-12-28 | BarnsleyvChesterfieldLeague One · England | 0–1 | League One · England |
| 2003-12-26 | ChesterfieldvPeterboroLeague One · England | 2–1 | League One · England |
| 2003-12-20 | Sheffield WedsvChesterfieldLeague One · England | 0–0 | League One · England |
| 2003-12-13 | ChesterfieldvTranmereLeague One · England | 2–2 | League One · England |
| 2003-11-29 | LutonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2003-11-22 | ChesterfieldvOldhamLeague One · England | 1–1 | League One · England |
| 2003-11-15 | BlackpoolvChesterfieldLeague One · England | 1–0 | League One · England |
| 2003-11-01 | ChesterfieldvPort ValeLeague One · England | 1–0 | League One · England |
| 2003-10-25 | ColchestervChesterfieldLeague One · England | 1–0 | League One · England |
| 2003-10-21 | ChesterfieldvHartlepoolLeague One · England | 1–2 | League One · England |
| 2003-10-18 | ChesterfieldvSwindonLeague One · England | 3–0 | League One · England |
| 2003-10-11 | Rushden & DvChesterfieldLeague One · England | 2–1 | League One · England |
| 2003-10-04 | StockportvChesterfieldLeague One · England | 0–0 | League One · England |
| 2003-09-30 | ChesterfieldvBournemouthLeague One · England | 1–1 | League One · England |
| 2003-09-27 | ChesterfieldvBrentfordLeague One · England | 1–2 | League One · England |
| 2003-09-20 | GrimsbyvChesterfieldLeague One · England | 4–0 | League One · England |
| 2003-09-16 | BrightonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2003-09-13 | ChesterfieldvNotts CountyLeague One · England | 0–1 | League One · England |
| 2003-09-06 | ChesterfieldvBarnsleyLeague One · England | 0–2 | League One · England |
| 2003-08-30 | QPRvChesterfieldLeague One · England | 3–0 | League One · England |
| 2003-08-25 | ChesterfieldvPlymouthLeague One · England | 1–1 | League One · England |
| 2003-08-23 | WycombevChesterfieldLeague One · England | 3–3 | League One · England |
| 2003-08-16 | ChesterfieldvBristol CityLeague One · England | 1–1 | League One · England |
| 2003-08-09 | WrexhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 2003-05-03 | BlackpoolvChesterfieldLeague One · England | 1–1 | League One · England |
| 2003-04-26 | ChesterfieldvBristol CityLeague One · England | 2–0 | League One · England |
| 2003-04-21 | ChesterfieldvBrentfordLeague One · England | 0–2 | League One · England |
| 2003-04-19 | OldhamvChesterfieldLeague One · England | 4–0 | League One · England |
| 2003-04-13 | ChesterfieldvCardiffLeague One · England | 0–3 | League One · England |
| 2003-04-05 | HuddersfieldvChesterfieldLeague One · England | 4–0 | League One · England |
| 2003-03-29 | TranmerevChesterfieldLeague One · England | 2–1 | League One · England |
| 2003-03-22 | ChesterfieldvWycombeLeague One · England | 4–0 | League One · England |
| 2003-03-18 | ChesterfieldvColchesterLeague One · England | 0–4 | League One · England |
| 2003-03-15 | Notts CountyvChesterfieldLeague One · England | 1–1 | League One · England |
| 2003-03-08 | ChesterfieldvPlymouthLeague One · England | 3–2 | League One · England |
| 2003-03-04 | StockportvChesterfieldLeague One · England | 2–1 | League One · England |
| 2003-03-01 | WiganvChesterfieldLeague One · England | 3–1 | League One · England |
| 2003-02-22 | ChesterfieldvCreweLeague One · England | 0–2 | League One · England |
| 2003-02-15 | BarnsleyvChesterfieldLeague One · England | 2–1 | League One · England |
| 2003-02-11 | Port ValevChesterfieldLeague One · England | 5–2 | League One · England |
| 2003-02-08 | ChesterfieldvPeterboroLeague One · England | 0–0 | League One · England |
| 2003-02-02 | ChesterfieldvQPRLeague One · England | 2–4 | League One · England |
| 2003-01-25 | CheltenhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 2003-01-18 | ChesterfieldvMansfieldLeague One · England | 1–2 | League One · England |
| 2003-01-04 | SwindonvChesterfieldLeague One · England | 3–0 | League One · England |
| 2003-01-01 | ChesterfieldvLutonLeague One · England | 2–1 | League One · England |