| 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 |
| 1995-05-06 | Leyton OrientvWycombeLeague One · England | 0–1 | League One · England |
| 1995-04-29 | ChestervLeyton OrientLeague One · England | 1–0 | League One · England |
| 1995-04-22 | Bristol RvsvLeyton OrientLeague One · England | 1–0 | League One · England |
| 1995-04-17 | Leyton OrientvBrentfordLeague One · England | 0–2 | League One · England |
| 1995-04-15 | SwanseavLeyton OrientLeague One · England | 2–0 | League One · England |
| 1995-04-11 | Leyton OrientvBristol RvsLeague One · England | 1–2 | League One · England |
| 1995-04-08 | Leyton OrientvCreweLeague One · England | 1–4 | League One · England |
| 1995-04-04 | CardiffvLeyton OrientLeague One · England | 2–1 | League One · England |
| 1995-04-01 | BournemouthvLeyton OrientLeague One · England | 2–0 | League One · England |
| 1995-03-25 | Leyton OrientvShrewsburyLeague One · England | 2–1 | League One · England |
| 1995-03-21 | CambridgevLeyton OrientLeague One · England | 0–0 | League One · England |
| 1995-03-18 | Leyton OrientvHuddersfieldLeague One · England | 0–2 | League One · England |
| 1995-03-11 | HullvLeyton OrientLeague One · England | 2–0 | League One · England |
| 1995-03-07 | Leyton OrientvBrightonLeague One · England | 0–3 | League One · England |
| 1995-03-04 | Leyton OrientvOxfordLeague One · England | 1–1 | League One · England |
| 1995-02-25 | PlymouthvLeyton OrientLeague One · England | 1–0 | League One · England |
| 1995-02-21 | YorkvLeyton OrientLeague One · England | 4–1 | League One · England |
| 1995-02-18 | Leyton OrientvWrexhamLeague One · England | 1–1 | League One · England |
| 1995-02-04 | Leyton OrientvPeterboroLeague One · England | 4–1 | League One · England |
| 1995-02-01 | Leyton OrientvBlackpoolLeague One · England | 0–1 | League One · England |
| 1995-01-28 | StockportvLeyton OrientLeague One · England | 2–1 | League One · England |
| 1995-01-14 | WrexhamvLeyton OrientLeague One · England | 4–1 | League One · England |
| 1995-01-07 | Leyton OrientvRotherhamLeague One · England | 0–0 | League One · England |