| 2006-09-02 | Nott'm ForestvChesterfieldLeague One · England | 4–0 | League One · England |
| 2006-08-26 | ChesterfieldvTranmereLeague One · England | 0–2 | League One · England |
| 2006-08-19 | Port ValevChesterfieldLeague One · England | 3–2 | League One · England |
| 2006-08-12 | ChesterfieldvMillwallLeague One · England | 5–1 | League One · England |
| 2006-08-09 | ChesterfieldvCarlisleLeague One · England | 0–0 | League One · England |
| 2006-08-05 | BournemouthvChesterfieldLeague One · England | 0–3 | League One · England |
| 2006-05-06 | ChesterfieldvSwanseaLeague One · England | 0–4 | League One · England |
| 2006-04-29 | Port ValevChesterfieldLeague One · England | 3–1 | League One · England |
| 2006-04-22 | ChesterfieldvMilton Keynes DonsLeague One · England | 1–2 | League One · England |
| 2006-04-18 | HuddersfieldvChesterfieldLeague One · England | 1–2 | League One · England |
| 2006-04-15 | ChesterfieldvColchesterLeague One · England | 2–2 | League One · England |
| 2006-04-08 | BarnsleyvChesterfieldLeague One · England | 1–1 | League One · England |
| 2006-04-01 | ChesterfieldvNott'm ForestLeague One · England | 1–3 | League One · England |
| 2006-03-25 | SwindonvChesterfieldLeague One · England | 2–0 | League One · England |
| 2006-03-18 | ChesterfieldvScunthorpeLeague One · England | 1–2 | League One · England |
| 2006-03-11 | TranmerevChesterfieldLeague One · England | 4–1 | League One · England |
| 2006-03-04 | ChesterfieldvYeovilLeague One · England | 0–3 | League One · England |
| 2006-02-25 | RotherhamvChesterfieldLeague One · England | 0–4 | League One · England |
| 2006-02-18 | ChesterfieldvSouthendLeague One · England | 3–4 | League One · England |
| 2006-02-15 | ChesterfieldvDoncasterLeague One · England | 0–1 | League One · England |
| 2006-02-10 | HartlepoolvChesterfieldLeague One · England | 1–0 | League One · England |
| 2006-02-04 | ChesterfieldvGillinghamLeague One · England | 1–1 | League One · England |
| 2006-01-28 | BournemouthvChesterfieldLeague One · England | 1–2 | League One · England |
| 2006-01-21 | ChesterfieldvWalsallLeague One · England | 2–2 | League One · England |
| 2006-01-14 | DoncastervChesterfieldLeague One · England | 1–1 | League One · England |
| 2006-01-07 | ChesterfieldvBradfordLeague One · England | 1–0 | League One · England |
| 2006-01-02 | ChesterfieldvBarnsleyLeague One · England | 0–0 | League One · England |
| 2005-12-31 | Nott'm ForestvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-12-28 | ChesterfieldvSwindonLeague One · England | 1–1 | League One · England |
| 2005-12-26 | ScunthorpevChesterfieldLeague One · England | 2–2 | League One · England |
| 2005-12-17 | ChesterfieldvOldhamLeague One · England | 1–1 | League One · England |
| 2005-12-10 | BrentfordvChesterfieldLeague One · England | 1–1 | League One · England |
| 2005-12-06 | SouthendvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-11-26 | ChesterfieldvBlackpoolLeague One · England | 1–1 | League One · England |
| 2005-11-19 | Bristol CityvChesterfieldLeague One · England | 2–4 | League One · England |
| 2005-11-12 | ChesterfieldvPort ValeLeague One · England | 2–0 | League One · England |
| 2005-10-29 | SwanseavChesterfieldLeague One · England | 5–1 | League One · England |
| 2005-10-26 | ChesterfieldvBristol CityLeague One · England | 3–0 | League One · England |
| 2005-10-22 | ChesterfieldvHuddersfieldLeague One · England | 4–3 | League One · England |
| 2005-10-15 | Milton Keynes DonsvChesterfieldLeague One · England | 0–0 | League One · England |
| 2005-10-01 | ColchestervChesterfieldLeague One · England | 1–2 | League One · England |
| 2005-09-27 | GillinghamvChesterfieldLeague One · England | 1–0 | League One · England |
| 2005-09-24 | ChesterfieldvHartlepoolLeague One · England | 3–1 | League One · England |
| 2005-09-17 | WalsallvChesterfieldLeague One · England | 2–3 | League One · England |
| 2005-09-10 | ChesterfieldvBournemouthLeague One · England | 3–0 | League One · England |
| 2005-09-02 | BradfordvChesterfieldLeague One · England | 2–0 | League One · England |
| 2005-08-29 | YeovilvChesterfieldLeague One · England | 1–3 | League One · England |
| 2005-08-27 | ChesterfieldvTranmereLeague One · England | 0–2 | League One · England |
| 2005-08-20 | OldhamvChesterfieldLeague One · England | 4–1 | League One · England |
| 2005-08-13 | ChesterfieldvRotherhamLeague One · England | 0–1 | League One · England |