| 1999-02-06 | CarlislevLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1999-01-30 | Leyton OrientvDarlingtonLeague Two · England | 3–2 | League Two · England |
| 1999-01-16 | RotherhamvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 1999-01-09 | Leyton OrientvChesterLeague Two · England | 2–2 | League Two · England |
| 1998-12-28 | DarlingtonvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-12-26 | Leyton OrientvSwanseaLeague Two · England | 1–1 | League Two · England |
| 1998-12-19 | BarnetvLeyton OrientLeague Two · England | 3–2 | League Two · England |
| 1998-12-12 | Leyton OrientvPeterboroLeague Two · England | 1–2 | League Two · England |
| 1998-11-28 | PlymouthvLeyton OrientLeague Two · England | 2–4 | League Two · England |
| 1998-11-21 | Leyton OrientvBrentfordLeague Two · England | 2–1 | League Two · England |
| 1998-11-10 | ShrewsburyvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-11-07 | HullvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 1998-10-31 | Leyton OrientvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1998-10-24 | Leyton OrientvHalifaxLeague Two · England | 1–0 | League Two · England |
| 1998-10-20 | CardiffvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 1998-10-17 | SouthendvLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 1998-10-09 | Leyton OrientvExeterLeague Two · England | 2–0 | League Two · England |
| 1998-10-03 | Leyton OrientvHartlepoolLeague Two · England | 1–1 | League Two · England |
| 1998-09-27 | RochdalevLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1998-09-19 | Leyton OrientvBrightonLeague Two · England | 1–0 | League Two · England |
| 1998-09-12 | CambridgevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1998-09-08 | Leyton OrientvMansfieldLeague Two · England | 1–1 | League Two · England |
| 1998-09-05 | Leyton OrientvCarlisleLeague Two · England | 2–1 | League Two · England |
| 1998-09-01 | TorquayvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-08-29 | Leyton OrientvScarboroughLeague Two · England | 0–3 | League Two · England |
| 1998-08-22 | SwanseavLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-08-15 | Leyton OrientvRotherhamLeague Two · England | 1–4 | League Two · England |
| 1998-08-08 | ChestervLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 1998-05-02 | Leyton OrientvTorquayLeague Two · England | 2–1 | League Two · England |
| 1998-04-25 | ColchestervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-04-21 | Leyton OrientvScunthorpeLeague Two · England | 1–0 | League Two · England |
| 1998-04-18 | HullvLeyton OrientLeague Two · England | 3–2 | League Two · England |
| 1998-04-13 | Leyton OrientvShrewsburyLeague Two · England | 2–3 | League Two · England |
| 1998-04-11 | BarnetvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 1998-04-04 | Leyton OrientvMansfieldLeague Two · England | 2–2 | League Two · England |
| 1998-03-29 | Notts CountyvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1998-03-21 | Leyton OrientvDarlingtonLeague Two · England | 2–0 | League Two · England |
| 1998-03-14 | ScarboroughvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 1998-03-07 | Leyton OrientvLincolnLeague Two · England | 1–0 | League Two · England |
| 1998-03-03 | ChestervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 1998-02-28 | RotherhamvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 1998-02-24 | Leyton OrientvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 1998-02-21 | Leyton OrientvSwanseaLeague Two · England | 2–2 | League Two · England |
| 1998-02-14 | MacclesfieldvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1998-02-06 | Leyton OrientvPeterboroLeague Two · England | 1–0 | League Two · England |
| 1998-01-31 | ExetervLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 1998-01-24 | RochdalevLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 1998-01-17 | Leyton OrientvBrightonLeague Two · England | 3–1 | League Two · England |
| 1998-01-10 | CardiffvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 1997-12-28 | Leyton OrientvDoncasterLeague Two · England | 8–0 | League Two · England |