| 2002-03-05 | ChesterfieldvHuddersfieldLeague One · England | 1–1 | League One · England |
| 2002-03-02 | WrexhamvChesterfieldLeague One · England | 0–1 | League One · England |
| 2002-02-26 | SwindonvChesterfieldLeague One · England | 2–1 | League One · England |
| 2002-02-23 | ChesterfieldvNorthamptonLeague One · England | 2–2 | League One · England |
| 2002-02-16 | Port ValevChesterfieldLeague One · England | 4–1 | League One · England |
| 2002-02-12 | ChesterfieldvWycombeLeague One · England | 0–1 | League One · England |
| 2002-02-09 | ChesterfieldvBuryLeague One · England | 2–0 | League One · England |
| 2002-02-05 | PeterborovChesterfieldLeague One · England | 1–1 | League One · England |
| 2002-02-02 | TranmerevChesterfieldLeague One · England | 0–0 | League One · England |
| 2002-01-21 | ChesterfieldvBrightonLeague One · England | 1–2 | League One · England |
| 2002-01-19 | ColchestervChesterfieldLeague One · England | 1–2 | League One · England |
| 2002-01-12 | ChesterfieldvOldhamLeague One · England | 4–2 | League One · England |
| 2001-12-29 | ChesterfieldvNotts CountyLeague One · England | 2–1 | League One · England |
| 2001-12-21 | BrightonvChesterfieldLeague One · England | 2–2 | League One · England |
| 2001-12-15 | ChesterfieldvQPRLeague One · England | 2–3 | League One · England |
| 2001-12-01 | ReadingvChesterfieldLeague One · England | 0–1 | League One · England |
| 2001-11-24 | ChesterfieldvBournemouthLeague One · England | 2–1 | League One · England |
| 2001-11-20 | WiganvChesterfieldLeague One · England | 1–1 | League One · England |
| 2001-11-10 | CardiffvChesterfieldLeague One · England | 2–1 | League One · England |
| 2001-11-03 | ChesterfieldvCambridgeLeague One · England | 2–0 | League One · England |
| 2001-10-27 | BlackpoolvChesterfieldLeague One · England | 1–0 | League One · England |
| 2001-10-23 | ChesterfieldvStokeLeague One · England | 1–2 | League One · England |
| 2001-10-20 | BuryvChesterfieldLeague One · England | 2–1 | League One · England |
| 2001-10-13 | ChesterfieldvPort ValeLeague One · England | 1–1 | League One · England |
| 2001-10-05 | Bristol CityvChesterfieldLeague One · England | 3–0 | League One · England |
| 2001-09-29 | ChesterfieldvTranmereLeague One · England | 0–2 | League One · England |
| 2001-09-25 | HuddersfieldvChesterfieldLeague One · England | 0–0 | League One · England |
| 2001-09-22 | ChesterfieldvSwindonLeague One · England | 4–0 | League One · England |
| 2001-09-18 | ChesterfieldvWrexhamLeague One · England | 3–2 | League One · England |
| 2001-09-15 | NorthamptonvChesterfieldLeague One · England | 0–2 | League One · England |
| 2001-09-08 | WycombevChesterfieldLeague One · England | 0–0 | League One · England |
| 2001-09-01 | ChesterfieldvPeterboroLeague One · England | 0–1 | League One · England |
| 2001-08-27 | Notts CountyvChesterfieldLeague One · England | 1–1 | League One · England |
| 2001-08-25 | ChesterfieldvBrentfordLeague One · England | 0–1 | League One · England |
| 2001-08-18 | OldhamvChesterfieldLeague One · England | 1–1 | League One · England |
| 2001-08-11 | ChesterfieldvColchesterLeague One · England | 3–6 | League One · England |
| 2001-05-05 | ChesterfieldvHalifaxLeague Two · England | 3–0 | League Two · England |
| 2001-05-01 | BrightonvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2001-04-28 | HullvChesterfieldLeague Two · England | 3–1 | League Two · England |
| 2001-04-21 | ChesterfieldvLincolnLeague Two · England | 1–2 | League Two · England |
| 2001-04-16 | CardiffvChesterfieldLeague Two · England | 3–3 | League Two · England |
| 2001-04-14 | ChesterfieldvKidderminsterLeague Two · England | 1–0 | League Two · England |
| 2001-04-07 | Leyton OrientvChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2001-03-31 | ChesterfieldvSouthendLeague Two · England | 1–1 | League Two · England |
| 2001-03-17 | ChesterfieldvRochdaleLeague Two · England | 1–1 | League Two · England |
| 2001-03-10 | PlymouthvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2001-03-03 | MacclesfieldvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2001-02-24 | ChesterfieldvBlackpoolLeague Two · England | 2–1 | League Two · England |
| 2001-02-20 | ChesterfieldvCarlisleLeague Two · England | 1–1 | League Two · England |
| 2001-02-17 | MansfieldvChesterfieldLeague Two · England | 0–1 | League Two · England |