| 2019-12-29 | Newport CountyvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2019-12-26 | Leyton OrientvColchesterLeague Two · England | 1–3 | League Two · England |
| 2019-12-21 | CambridgevLeyton OrientLeague Two · England | 2–3 | League Two · England |
| 2019-12-14 | Leyton OrientvBradfordLeague Two · England | 0–0 | League Two · England |
| 2019-12-07 | OldhamvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2019-11-23 | Leyton OrientvForest GreenLeague Two · England | 2–4 | League Two · England |
| 2019-11-16 | Leyton OrientvScunthorpeLeague Two · England | 0–2 | League Two · England |
| 2019-11-02 | MorecambevLeyton OrientLeague Two · England | 1–0 | League Two · England |
| 2019-10-26 | Leyton OrientvCarlisleLeague Two · England | 1–1 | League Two · England |
| 2019-10-22 | PlymouthvLeyton OrientLeague Two · England | 4–0 | League Two · England |
| 2019-10-19 | GrimsbyvLeyton OrientLeague Two · England | 0–4 | League Two · England |
| 2019-10-12 | Leyton OrientvWalsallLeague Two · England | 3–1 | League Two · England |
| 2019-10-05 | NorthamptonvLeyton OrientLeague Two · England | 0–1 | League Two · England |
| 2019-09-28 | Leyton OrientvPort ValeLeague Two · England | 3–3 | League Two · England |
| 2019-09-21 | ColchestervLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 2019-09-17 | Leyton OrientvCreweLeague Two · England | 1–2 | League Two · England |
| 2019-09-14 | ExetervLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 2019-09-07 | Leyton OrientvSwindonLeague Two · England | 1–3 | League Two · England |
| 2019-08-31 | SalfordvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2019-08-24 | Leyton OrientvCrawley TownLeague Two · England | 2–3 | League Two · England |
| 2019-08-20 | MansfieldvLeyton OrientLeague Two · England | 2–3 | League Two · England |
| 2019-08-17 | Leyton OrientvStevenageLeague Two · England | 0–0 | League Two · England |
| 2019-08-10 | MacclesfieldvLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 2019-08-03 | Leyton OrientvCheltenhamLeague Two · England | 1–0 | League Two · England |