| 2007-11-03 | ChesterfieldvMorecambeLeague Two · England | 2–2 | League Two · England |
| 2007-10-27 | DarlingtonvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2007-10-20 | ChesterfieldvDag and RedLeague Two · England | 1–1 | League Two · England |
| 2007-10-13 | ShrewsburyvChesterfieldLeague Two · England | 2–3 | League Two · England |
| 2007-10-06 | ChesterfieldvMacclesfieldLeague Two · England | 2–2 | League Two · England |
| 2007-10-02 | WrexhamvChesterfieldLeague Two · England | 0–4 | League Two · England |
| 2007-09-29 | Notts CountyvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2007-09-22 | ChesterfieldvBarnetLeague Two · England | 0–1 | League Two · England |
| 2007-09-15 | MansfieldvChesterfieldLeague Two · England | 1–3 | League Two · England |
| 2007-09-07 | ChesterfieldvBuryLeague Two · England | 3–1 | League Two · England |
| 2007-09-01 | ChesterfieldvWycombeLeague Two · England | 2–0 | League Two · England |
| 2007-08-25 | PeterborovChesterfieldLeague Two · England | 2–3 | League Two · England |
| 2007-08-18 | ChesterfieldvStockportLeague Two · England | 1–1 | League Two · England |
| 2007-08-11 | ChestervChesterfieldLeague Two · England | 0–0 | League Two · 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 |
| 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 |
| 2000-12-26 | ChesterfieldvDarlingtonLeague Two · England | 2–0 | League Two · England |
| 2000-12-23 | TorquayvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2000-12-16 | SouthendvChesterfieldLeague Two · England | 3–2 | League Two · England |
| 2000-12-09 | ChesterfieldvExeterLeague Two · England | 2–0 | League Two · England |
| 2000-12-02 | ChesterfieldvLeyton OrientLeague Two · England | 4–1 | League Two · England |
| 2000-11-25 | HalifaxvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2000-11-11 | ChesterfieldvHullLeague Two · England | 1–0 | League Two · England |
| 2000-11-04 | LincolnvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2000-10-28 | ChesterfieldvCardiffLeague Two · England | 2–2 | League Two · England |
| 2000-10-24 | KidderminstervChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2000-10-21 | ChesterfieldvBrightonLeague Two · England | 1–0 | League Two · England |
| 2000-10-17 | RochdalevChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2000-10-14 | ExetervChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2000-10-07 | ChesterfieldvPlymouthLeague Two · England | 2–1 | League Two · England |