| 1995-12-30 | ExetervChesterLeague Two · England | 1–2 | League Two · England |
| 1995-12-26 | CardiffvChesterLeague Two · England | 0–0 | League Two · England |
| 1995-12-23 | ChestervBarnetLeague Two · England | 0–2 | League Two · England |
| 1995-12-16 | ChestervPrestonLeague Two · England | 1–1 | League Two · England |
| 1995-11-25 | ChestervDarlingtonLeague Two · England | 4–1 | League Two · England |
| 1995-11-18 | MansfieldvChesterLeague Two · England | 3–4 | League Two · England |
| 1995-11-04 | ChestervTorquayLeague Two · England | 4–1 | League Two · England |
| 1995-10-31 | RochdalevChesterLeague Two · England | 1–3 | League Two · England |
| 1995-10-28 | ScarboroughvChesterLeague Two · England | 0–0 | League Two · England |
| 1995-10-21 | ChestervFulhamLeague Two · England | 1–1 | League Two · England |
| 1995-10-14 | Leyton OrientvChesterLeague Two · England | 0–2 | League Two · England |
| 1995-10-07 | ChestervDoncasterLeague Two · England | 0–3 | League Two · England |
| 1995-09-30 | PrestonvChesterLeague Two · England | 2–0 | League Two · England |
| 1995-09-23 | ChestervGillinghamLeague Two · England | 1–1 | League Two · England |
| 1995-09-16 | ChestervLincolnLeague Two · England | 5–1 | League Two · England |
| 1995-09-12 | ScunthorpevChesterLeague Two · England | 0–2 | League Two · England |
| 1995-09-09 | ColchestervChesterLeague Two · England | 1–2 | League Two · England |
| 1995-09-02 | ChestervHerefordLeague Two · England | 2–1 | League Two · England |
| 1995-08-29 | WiganvChesterLeague Two · England | 2–1 | League Two · England |
| 1995-08-26 | ChestervPlymouthLeague Two · England | 3–1 | League Two · England |
| 1995-08-19 | BuryvChesterLeague Two · England | 1–1 | League Two · England |
| 1995-08-12 | ChestervHartlepoolLeague Two · England | 2–0 | League Two · England |