| 2023-05-08 | BradfordvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2023-04-29 | Leyton OrientvStockportLeague Two · England | 0–3 | League Two · England |
| 2023-04-25 | MansfieldvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 2023-04-22 | Leyton OrientvCreweLeague Two · England | 2–0 | League Two · England |
| 2023-04-18 | GillinghamvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 2023-04-15 | SuttonvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2023-04-10 | Leyton OrientvHarrogateLeague Two · England | 2–2 | League Two · England |
| 2023-04-07 | SalfordvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2023-04-01 | Leyton OrientvCarlisleLeague Two · England | 1–0 | League Two · England |
| 2023-03-25 | HartlepoolvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2023-03-18 | Leyton OrientvColchesterLeague Two · England | 2–2 | League Two · England |
| 2023-03-04 | Leyton OrientvSwindonLeague Two · England | 1–1 | League Two · England |
| 2023-02-25 | GrimsbyvLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 2023-02-18 | Leyton OrientvCrawley TownLeague Two · England | 1–0 | League Two · England |
| 2023-02-14 | Leyton OrientvRochdaleLeague Two · England | 2–1 | League Two · England |
| 2023-02-11 | WalsallvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2023-02-07 | CrewevLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2023-02-04 | Leyton OrientvAFC WimbledonLeague Two · England | 1–0 | League Two · England |
| 2023-01-28 | TranmerevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 2023-01-21 | StevenagevLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 2023-01-14 | Leyton OrientvBarrowLeague Two · England | 0–0 | League Two · England |
| 2023-01-07 | Leyton OrientvDoncasterLeague Two · England | 1–0 | League Two · England |
| 2023-01-02 | NorthamptonvLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 2022-12-30 | Newport CountyvLeyton OrientLeague Two · England | 0–0 | League Two · England |
| 2022-12-27 | Leyton OrientvStevenageLeague Two · England | 0–0 | League Two · England |
| 2022-12-17 | Leyton OrientvSuttonLeague Two · England | 2–0 | League Two · England |
| 2022-12-03 | Leyton OrientvBradfordLeague Two · England | 3–0 | League Two · England |
| 2022-11-19 | StockportvLeyton OrientLeague Two · England | 1–2 | League Two · England |
| 2022-11-12 | HarrogatevLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2022-11-08 | AFC WimbledonvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 2022-10-29 | Leyton OrientvSalfordLeague Two · England | 1–0 | League Two · England |
| 2022-10-25 | Leyton OrientvGillinghamLeague Two · England | 2–0 | League Two · England |
| 2022-10-22 | CarlislevLeyton OrientLeague Two · England | 2–3 | League Two · England |
| 2022-10-15 | Leyton OrientvNorthamptonLeague Two · England | 0–0 | League Two · England |
| 2022-10-08 | DoncastervLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2022-10-01 | Leyton OrientvNewport CountyLeague Two · England | 1–2 | League Two · England |
| 2022-09-24 | BarrowvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2022-09-17 | Leyton OrientvWalsallLeague Two · England | 1–0 | League Two · England |
| 2022-09-13 | RochdalevLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 2022-09-03 | Leyton OrientvTranmereLeague Two · England | 2–0 | League Two · England |
| 2022-08-27 | Leyton OrientvHartlepoolLeague Two · England | 4–2 | League Two · England |
| 2022-08-20 | ColchestervLeyton OrientLeague Two · England | 1–3 | League Two · England |
| 2022-08-16 | SwindonvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2022-08-13 | Leyton OrientvMansfieldLeague Two · England | 1–0 | League Two · England |
| 2022-08-06 | Crawley TownvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 2022-07-30 | Leyton OrientvGrimsbyLeague Two · England | 2–0 | League Two · England |
| 2022-05-07 | Leyton OrientvTranmereLeague Two · England | 0–1 | League Two · England |
| 2022-04-30 | Crawley TownvLeyton OrientLeague Two · England | 0–2 | League Two · England |
| 2022-04-23 | Leyton OrientvNorthamptonLeague Two · England | 2–4 | League Two · England |
| 2022-04-18 | SwindonvLeyton OrientLeague Two · England | 1–2 | League Two · England |