| 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 |
| 2001-02-09 | ChesterfieldvCheltenhamLeague Two · England | 2–0 | League Two · England |
| 2001-02-03 | BarnetvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2001-01-27 | ChesterfieldvTorquayLeague Two · England | 3–0 | League Two · England |
| 2001-01-23 | YorkvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2001-01-20 | DarlingtonvChesterfieldLeague Two · England | 0–3 | League Two · England |
| 2001-01-16 | ChesterfieldvHartlepoolLeague Two · England | 0–0 | League Two · England |
| 2001-01-13 | ChesterfieldvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 2001-01-06 | ShrewsburyvChesterfieldLeague Two · England | 0–0 | League Two · England |