| 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 |
| 2007-05-05 | OldhamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2007-04-28 | ChesterfieldvBradfordLeague One · England | 3–0 | League One · England |
| 2007-04-21 | NorthamptonvChesterfieldLeague One · England | 1–0 | League One · England |
| 2007-04-14 | ChesterfieldvGillinghamLeague One · England | 0–1 | League One · England |
| 2007-04-09 | CheltenhamvChesterfieldLeague One · England | 0–0 | League One · England |
| 2007-04-07 | ChesterfieldvCreweLeague One · England | 2–1 | League One · England |
| 2007-03-24 | YeovilvChesterfieldLeague One · England | 1–0 | League One · England |
| 2007-03-21 | ChesterfieldvDoncasterLeague One · England | 1–1 | League One · England |
| 2007-03-16 | SwanseavChesterfieldLeague One · England | 2–0 | League One · England |
| 2007-03-10 | ChesterfieldvLeyton OrientLeague One · England | 0–1 | League One · England |
| 2007-03-07 | ChesterfieldvBristol CityLeague One · England | 1–3 | League One · England |
| 2007-03-02 | TranmerevChesterfieldLeague One · England | 2–0 | League One · England |
| 2007-02-24 | ChesterfieldvNott'm ForestLeague One · England | 1–2 | League One · England |
| 2007-02-20 | CarlislevChesterfieldLeague One · England | 0–0 | League One · England |
| 2007-02-17 | ChesterfieldvPort ValeLeague One · England | 3–0 | League One · England |
| 2007-02-10 | MillwallvChesterfieldLeague One · England | 2–1 | League One · England |
| 2007-02-03 | ChesterfieldvBournemouthLeague One · England | 0–1 | League One · England |
| 2007-01-27 | HuddersfieldvChesterfieldLeague One · England | 1–1 | League One · England |
| 2007-01-20 | ChesterfieldvBrightonLeague One · England | 0–1 | League One · England |
| 2007-01-13 | RotherhamvChesterfieldLeague One · England | 0–1 | League One · England |
| 2007-01-01 | ChesterfieldvBlackpoolLeague One · England | 2–0 | League One · England |