| 2000-02-19 | Leyton OrientvCheltenhamLeague Two · England | 1–0 | League Two · England |
| 2000-02-12 | ShrewsburyvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 2000-02-08 | Leyton OrientvExeterLeague Two · England | 4–1 | League Two · England |
| 2000-02-05 | Leyton OrientvSouthendLeague Two · England | 2–1 | League Two · England |
| 2000-01-29 | HalifaxvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2000-01-22 | Leyton OrientvPeterboroLeague Two · England | 1–1 | League Two · England |
| 2000-01-15 | BrightonvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 2000-01-08 | ExetervLeyton OrientLeague Two · England | 1–3 | League Two · England |
| 2000-01-03 | Leyton OrientvHullLeague Two · England | 0–0 | League Two · England |
| 1999-12-28 | ChestervLeyton OrientLeague Two · England | 1–5 | League Two · England |
| 1999-12-26 | Leyton OrientvSwanseaLeague Two · England | 0–1 | League Two · England |
| 1999-12-18 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-12-04 | Leyton OrientvCarlisleLeague Two · England | 0–1 | League Two · England |
| 1999-11-27 | CheltenhamvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1999-11-23 | Leyton OrientvRochdaleLeague Two · England | 0–0 | League Two · England |
| 1999-11-12 | RotherhamvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 1999-11-06 | Leyton OrientvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 1999-11-02 | DarlingtonvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-10-23 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-10-19 | Leyton OrientvBarnetLeague Two · England | 0–0 | League Two · England |
| 1999-10-16 | Leyton OrientvLincolnLeague Two · England | 2–3 | League Two · England |
| 1999-10-09 | YorkvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-10-02 | PlymouthvLeyton OrientLeague Two · England | 5–0 | League Two · England |
| 1999-09-25 | Leyton OrientvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1999-09-18 | Leyton OrientvTorquayLeague Two · England | 0–2 | League Two · England |
| 1999-09-11 | MansfieldvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-09-03 | Leyton OrientvShrewsburyLeague Two · England | 1–2 | League Two · England |
| 1999-08-30 | SouthendvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-08-28 | Leyton OrientvHalifaxLeague Two · England | 1–0 | League Two · England |
| 1999-08-21 | PeterborovLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-08-14 | Leyton OrientvBrightonLeague Two · England | 1–2 | League Two · England |
| 1999-08-07 | CarlislevLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1999-05-08 | Leyton OrientvBarnetLeague Two · England | 2–2 | League Two · England |
| 1999-05-01 | PeterborovLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 1999-04-27 | HartlepoolvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1999-04-24 | Leyton OrientvShrewsburyLeague Two · England | 6–1 | League Two · England |
| 1999-04-21 | ScarboroughvLeyton OrientLeague Two · England | 1–3 | League Two · England |
| 1999-04-17 | BrentfordvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1999-04-13 | Leyton OrientvPlymouthLeague Two · England | 4–3 | League Two · England |
| 1999-04-10 | Leyton OrientvCardiffLeague Two · England | 1–1 | League Two · England |
| 1999-04-05 | ExetervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-04-03 | Leyton OrientvSouthendLeague Two · England | 0–3 | League Two · England |
| 1999-03-26 | HalifaxvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-03-20 | ScunthorpevLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1999-03-13 | Leyton OrientvHullLeague Two · England | 1–2 | League Two · England |
| 1999-03-06 | Leyton OrientvRochdaleLeague Two · England | 3–0 | League Two · England |
| 1999-03-02 | Leyton OrientvTorquayLeague Two · England | 2–0 | League Two · England |
| 1999-02-27 | BrightonvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1999-02-20 | Leyton OrientvCambridgeLeague Two · England | 2–0 | League Two · England |
| 1999-02-13 | MansfieldvLeyton OrientLeague Two · England | 1–2 | League Two · England |