| 1995-12-26 | ColchestervLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1995-12-22 | Leyton OrientvRochdaleLeague Two · England | 2–0 | League Two · England |
| 1995-12-16 | DoncastervLeyton OrientLeague Two · England | 4–1 | League Two · England |
| 1995-12-09 | Leyton OrientvExeterLeague Two · England | 0–3 | League Two · England |
| 1995-11-25 | BarnetvLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1995-11-18 | Leyton OrientvCambridgeLeague Two · England | 3–1 | League Two · England |
| 1995-11-04 | PrestonvLeyton OrientLeague Two · England | 4–0 | League Two · England |
| 1995-10-31 | Leyton OrientvHerefordLeague Two · England | 0–1 | League Two · England |
| 1995-10-28 | Leyton OrientvWiganLeague Two · England | 1–1 | League Two · England |
| 1995-10-21 | ScunthorpevLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1995-10-14 | Leyton OrientvChesterLeague Two · England | 0–2 | League Two · England |
| 1995-10-07 | BuryvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1995-09-30 | Leyton OrientvDoncasterLeague Two · England | 3–1 | League Two · England |
| 1995-09-23 | ExetervLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 1995-09-16 | Leyton OrientvHartlepoolLeague Two · England | 4–1 | League Two · England |
| 1995-09-12 | NorthamptonvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1995-09-09 | PlymouthvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1995-09-02 | Leyton OrientvFulhamLeague Two · England | 1–0 | League Two · England |
| 1995-08-30 | ScarboroughvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1995-08-26 | Leyton OrientvDarlingtonLeague Two · England | 1–1 | League Two · England |
| 1995-08-19 | MansfieldvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1995-08-12 | Leyton OrientvTorquayLeague Two · England | 1–0 | League Two · England |