| 2009-05-02 | ChestervDarlingtonLeague Two · England | 1–2 | League Two · England |
| 2009-04-25 | AldershotvChesterLeague Two · England | 2–2 | League Two · England |
| 2009-04-18 | ChestervBournemouthLeague Two · England | 0–2 | League Two · England |
| 2009-04-13 | AccringtonvChesterLeague Two · England | 0–1 | League Two · England |
| 2009-04-11 | ChestervMacclesfieldLeague Two · England | 0–2 | League Two · England |
| 2009-04-04 | Notts CountyvChesterLeague Two · England | 1–2 | League Two · England |
| 2009-03-28 | ChestervBradfordLeague Two · England | 0–0 | League Two · England |
| 2009-03-21 | BuryvChesterLeague Two · England | 1–1 | League Two · England |
| 2009-03-14 | ChestervGrimsbyLeague Two · England | 1–1 | League Two · England |
| 2009-03-10 | ChestervRotherhamLeague Two · England | 1–5 | League Two · England |
| 2009-03-07 | BarnetvChesterLeague Two · England | 3–1 | League Two · England |
| 2009-03-03 | WycombevChesterLeague Two · England | 2–0 | League Two · England |
| 2009-02-28 | ChestervDag and RedLeague Two · England | 2–2 | League Two · England |
| 2009-02-21 | ChestervExeterLeague Two · England | 0–0 | League Two · England |
| 2009-02-17 | ShrewsburyvChesterLeague Two · England | 1–0 | League Two · England |
| 2009-02-14 | MorecambevChesterLeague Two · England | 3–1 | League Two · England |
| 2009-02-07 | BrentfordvChesterLeague Two · England | 3–0 | League Two · England |
| 2009-02-03 | ChestervRochdaleLeague Two · England | 0–2 | League Two · England |
| 2009-01-31 | ChestervGillinghamLeague Two · England | 0–1 | League Two · England |
| 2009-01-27 | Port ValevChesterLeague Two · England | 3–0 | League Two · England |
| 2009-01-24 | LincolnvChesterLeague Two · England | 1–1 | League Two · England |
| 2009-01-17 | ChestervChesterfieldLeague Two · England | 1–3 | League Two · England |
| 2009-01-13 | ChestervLutonLeague Two · England | 2–2 | League Two · England |