| 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 |
| 1995-05-06 | SwanseavChesterLeague One · England | 0–1 | League One · England |
| 1995-04-29 | ChestervLeyton OrientLeague One · England | 1–0 | League One · England |
| 1995-04-22 | WycombevChesterLeague One · England | 3–1 | League One · England |
| 1995-04-17 | ChestervCreweLeague One · England | 0–1 | League One · England |
| 1995-04-15 | BrentfordvChesterLeague One · England | 1–1 | League One · England |
| 1995-04-08 | ChestervBristol RvsLeague One · England | 0–0 | League One · England |
| 1995-04-01 | CardiffvChesterLeague One · England | 2–1 | League One · England |
| 1995-03-28 | ChestervHullLeague One · England | 1–2 | League One · England |
| 1995-03-25 | ChestervBournemouthLeague One · England | 1–1 | League One · England |
| 1995-03-22 | BrightonvChesterLeague One · England | 1–0 | League One · England |
| 1995-03-18 | ChestervCambridgeLeague One · England | 1–3 | League One · England |
| 1995-03-11 | HuddersfieldvChesterLeague One · England | 5–1 | League One · England |
| 1995-03-04 | ChestervPlymouthLeague One · England | 1–0 | League One · England |
| 1995-02-25 | OxfordvChesterLeague One · England | 1–0 | League One · England |
| 1995-02-21 | BlackpoolvChesterLeague One · England | 3–1 | League One · England |
| 1995-02-18 | ChestervShrewsburyLeague One · England | 1–3 | League One · England |
| 1995-02-14 | WrexhamvChesterLeague One · England | 2–2 | League One · England |
| 1995-02-11 | StockportvChesterLeague One · England | 2–2 | League One · England |
| 1995-02-04 | ChestervRotherhamLeague One · England | 4–4 | League One · England |
| 1995-02-01 | ChestervWycombeLeague One · England | 0–2 | League One · England |
| 1995-01-28 | ChestervPeterboroLeague One · England | 1–1 | League One · England |
| 1995-01-14 | ShrewsburyvChesterLeague One · England | 1–0 | League One · England |
| 1995-01-07 | ChestervYorkLeague One · England | 0–4 | League One · England |