| 2011-05-07 | ChesterfieldvGillinghamLeague Two · England | 3–1 | League Two · England |
| 2011-04-29 | TorquayvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2011-04-25 | ChesterfieldvBuryLeague Two · England | 2–3 | League Two · England |
| 2011-04-23 | OxfordvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2011-04-16 | ChesterfieldvMacclesfieldLeague Two · England | 2–1 | League Two · England |
| 2011-04-09 | HerefordvChesterfieldLeague Two · England | 3–0 | League Two · England |
| 2011-04-02 | ChesterfieldvPort ValeLeague Two · England | 2–0 | League Two · England |
| 2011-03-26 | BarnetvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2011-03-18 | ChesterfieldvRotherhamLeague Two · England | 5–0 | League Two · England |
| 2011-03-12 | CrewevChesterfieldLeague Two · England | 2–0 | League Two · England |
| 2011-03-08 | ChesterfieldvNorthamptonLeague Two · England | 2–1 | League Two · England |
| 2011-03-05 | CheltenhamvChesterfieldLeague Two · England | 0–3 | League Two · England |
| 2011-03-01 | ChesterfieldvWycombeLeague Two · England | 4–1 | League Two · England |
| 2011-02-26 | ChesterfieldvMorecambeLeague Two · England | 0–2 | League Two · England |
| 2011-02-22 | BradfordvChesterfieldLeague Two · England | 0–1 | League Two · England |
| 2011-02-19 | LincolnvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2011-02-15 | BuryvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2011-02-11 | BurtonvChesterfieldLeague Two · England | 1–0 | League Two · England |
| 2011-02-05 | ChesterfieldvAldershotLeague Two · England | 2–2 | League Two · England |
| 2011-02-01 | StockportvChesterfieldLeague Two · England | 1–1 | League Two · England |
| 2011-01-29 | ChesterfieldvBradfordLeague Two · England | 2–2 | League Two · England |
| 2011-01-25 | GillinghamvChesterfieldLeague Two · England | 0–2 | League Two · England |
| 2011-01-22 | ShrewsburyvChesterfieldLeague Two · England | 0–0 | League Two · England |
| 2011-01-15 | ChesterfieldvStevenageLeague Two · England | 1–0 | League Two · England |
| 2011-01-08 | SouthendvChesterfieldLeague Two · England | 2–3 | League Two · England |
| 2011-01-03 | AccringtonvChesterfieldLeague Two · England | 2–2 | League Two · England |
| 2011-01-01 | ChesterfieldvStockportLeague Two · England | 4–1 | League Two · England |