| 2023-12-29 | Leyton OrientvWycombeLeague One · England | 0–0 | League One · England |
| 2023-12-26 | Leyton OrientvCharltonLeague One · England | 1–0 | League One · England |
| 2023-12-23 | BoltonvLeyton OrientLeague One · England | 3–2 | League One · England |
| 2023-12-16 | CheltenhamvLeyton OrientLeague One · England | 1–2 | League One · England |
| 2023-12-09 | Leyton OrientvDerbyLeague One · England | 0–3 | League One · England |
| 2023-11-28 | Bristol RvsvLeyton OrientLeague One · England | 1–1 | League One · England |
| 2023-11-25 | Leyton OrientvWiganLeague One · England | 1–1 | League One · England |
| 2023-11-21 | Leyton OrientvLincolnLeague One · England | 0–1 | League One · England |
| 2023-11-11 | Leyton OrientvOxfordLeague One · England | 2–3 | League One · England |
| 2023-10-28 | BurtonvLeyton OrientLeague One · England | 0–0 | League One · England |
| 2023-10-24 | NorthamptonvLeyton OrientLeague One · England | 2–2 | League One · England |
| 2023-10-21 | Leyton OrientvBarnsleyLeague One · England | 1–1 | League One · England |
| 2023-10-14 | CarlislevLeyton OrientLeague One · England | 0–1 | League One · England |
| 2023-10-07 | Leyton OrientvReadingLeague One · England | 2–1 | League One · England |
| 2023-09-30 | Fleetwood TownvLeyton OrientLeague One · England | 1–0 | League One · England |
| 2023-09-23 | Leyton OrientvShrewsburyLeague One · England | 1–0 | League One · England |
| 2023-09-16 | PeterborovLeyton OrientLeague One · England | 1–1 | League One · England |
| 2023-09-09 | ExetervLeyton OrientLeague One · England | 1–2 | League One · England |
| 2023-09-02 | Leyton OrientvStevenageLeague One · England | 0–3 | League One · England |
| 2023-08-26 | Leyton OrientvCambridgeLeague One · England | 2–0 | League One · England |
| 2023-08-19 | BlackpoolvLeyton OrientLeague One · England | 0–0 | League One · England |
| 2023-08-15 | WycombevLeyton OrientLeague One · England | 3–2 | League One · England |
| 2023-08-12 | Leyton OrientvPortsmouthLeague One · England | 0–4 | League One · England |
| 2023-08-05 | CharltonvLeyton OrientLeague One · England | 1–0 | League One · England |