| 1997-01-04 | Leyton OrientvMansfieldLeague Two · England | 2–1 | League Two · England |
| 1996-12-28 | DarlingtonvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-12-26 | Leyton OrientvNorthamptonLeague Two · England | 2–1 | League Two · England |
| 1996-12-22 | Leyton OrientvBrightonLeague Two · England | 2–0 | League Two · England |
| 1996-12-14 | FulhamvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-12-03 | BarnetvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1996-11-30 | Leyton OrientvCardiffLeague Two · England | 3–0 | League Two · England |
| 1996-11-23 | CambridgevLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1996-11-09 | ExetervLeyton OrientLeague Two · England | 3–2 | League Two · England |
| 1996-11-02 | Leyton OrientvTorquayLeague Two · England | 1–0 | League Two · England |
| 1996-10-29 | Leyton OrientvScarboroughLeague Two · England | 0–1 | League Two · England |
| 1996-10-26 | CardiffvLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1996-10-19 | HerefordvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1996-10-15 | Leyton OrientvChesterLeague Two · England | 0–0 | League Two · England |
| 1996-10-12 | Leyton OrientvHullLeague Two · England | 1–1 | League Two · England |
| 1996-10-05 | DoncastervLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1996-10-01 | Leyton OrientvSwanseaLeague Two · England | 1–0 | League Two · England |
| 1996-09-28 | RochdalevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1996-09-21 | Leyton OrientvColchesterLeague Two · England | 1–1 | League Two · England |
| 1996-09-14 | MansfieldvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 1996-09-10 | NorthamptonvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 1996-09-07 | Leyton OrientvDarlingtonLeague Two · England | 0–0 | League Two · England |
| 1996-08-31 | Leyton OrientvHartlepoolLeague Two · England | 2–0 | League Two · England |
| 1996-08-27 | CarlislevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1996-08-24 | LincolnvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-08-17 | Leyton OrientvScunthorpeLeague Two · England | 0–1 | League Two · England |
| 1996-05-04 | CambridgevLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1996-04-27 | Leyton OrientvBarnetLeague Two · England | 3–3 | League Two · England |
| 1996-04-20 | Leyton OrientvPrestonLeague Two · England | 0–2 | League Two · England |
| 1996-04-13 | HerefordvLeyton OrientLeague Two · England | 3–2 | League Two · England |
| 1996-04-08 | Leyton OrientvScunthorpeLeague Two · England | 0–0 | League Two · England |
| 1996-04-06 | WiganvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1996-04-02 | ChestervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-03-30 | Leyton OrientvBuryLeague Two · England | 0–2 | League Two · England |
| 1996-03-26 | FulhamvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1996-03-23 | GillinghamvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1996-03-19 | Leyton OrientvScarboroughLeague Two · England | 1–0 | League Two · England |
| 1996-03-16 | Leyton OrientvLincolnLeague Two · England | 2–0 | League Two · England |
| 1996-03-09 | RochdalevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1996-03-02 | Leyton OrientvColchesterLeague Two · England | 0–1 | League Two · England |
| 1996-02-27 | Leyton OrientvPlymouthLeague Two · England | 0–1 | League Two · England |
| 1996-02-24 | HartlepoolvLeyton OrientLeague Two · England | 4–1 | League Two · England |
| 1996-02-17 | Leyton OrientvNorthamptonLeague Two · England | 2–0 | League Two · England |
| 1996-02-10 | Leyton OrientvCardiffLeague Two · England | 4–1 | League Two · England |
| 1996-02-03 | DarlingtonvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1996-01-20 | TorquayvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1996-01-16 | LincolnvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1996-01-13 | Leyton OrientvMansfieldLeague Two · England | 1–0 | League Two · England |
| 1996-01-06 | CardiffvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1996-01-01 | Leyton OrientvGillinghamLeague Two · England | 0–1 | League Two · England |