| 2007-12-29 | BarnetvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2007-12-26 | BuryvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2007-12-22 | ChesterfieldvMansfieldLeague Two · England | 2–0 | League Two · England |
| 2007-12-15 | AccringtonvChesterfieldLeague Two · England | 2–1 | League Two · England |
| 2007-12-08 | ChesterfieldvBradfordLeague Two · England | 1–1 | League Two · England |
| 2007-12-05 | ChesterfieldvRotherhamLeague Two · England | 0–2 | League Two · England |
| 2007-11-24 | Milton Keynes DonsvChesterfieldLeague Two · England | 1–2 | League Two · England |
| 2007-11-06 | LincolnvChesterfieldLeague Two · England | 2–4 | League Two · England |
| 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 |