| 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 |
| 2017-05-06 | BlackpoolvLeyton OrientLeague Two · England | 3–1 | League Two · England |
| 2017-04-29 | Leyton OrientvColchesterLeague Two · England | 1–3 | League Two · England |
| 2017-04-22 | CrewevLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 2017-04-17 | Leyton OrientvHartlepoolLeague Two · England | 2–1 | League Two · England |
| 2017-04-14 | LutonvLeyton OrientLeague Two · England | 2–2 | League Two · England |
| 2017-04-08 | CambridgevLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 2017-04-01 | Leyton OrientvWycombeLeague Two · England | 0–2 | League Two · England |
| 2017-03-25 | Crawley TownvLeyton OrientLeague Two · England | 3–0 | League Two · England |
| 2017-03-18 | Leyton OrientvDoncasterLeague Two · England | 1–4 | League Two · England |
| 2017-03-14 | AccringtonvLeyton OrientLeague Two · England | 5–0 | League Two · England |
| 2017-03-11 | Leyton OrientvGrimsbyLeague Two · England | 0–3 | League Two · England |
| 2017-03-04 | Newport CountyvLeyton OrientLeague Two · England | 0–4 | League Two · England |
| 2017-02-28 | StevenagevLeyton OrientLeague Two · England | 4–1 | League Two · England |
| 2017-02-25 | Leyton OrientvCheltenhamLeague Two · England | 0–1 | League Two · England |
| 2017-02-18 | Leyton OrientvNotts CountyLeague Two · England | 2–3 | League Two · England |
| 2017-02-14 | PlymouthvLeyton OrientLeague Two · England | 2–3 | League Two · England |
| 2017-02-11 | YeovilvLeyton OrientLeague Two · England | 1–1 | League Two · England |
| 2017-02-07 | Leyton OrientvMorecambeLeague Two · England | 0–1 | League Two · England |
| 2017-02-04 | Leyton OrientvCarlisleLeague Two · England | 1–2 | League Two · England |
| 2017-01-28 | MansfieldvLeyton OrientLeague Two · England | 2–0 | League Two · England |
| 2017-01-14 | PortsmouthvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 2017-01-07 | Leyton OrientvBarnetLeague Two · England | 1–3 | League Two · England |
| 2017-01-02 | ExetervLeyton OrientLeague Two · England | 4–0 | League Two · England |
| 2016-12-31 | Leyton OrientvCambridgeLeague Two · England | 1–1 | League Two · England |
| 2016-12-26 | Leyton OrientvCrawley TownLeague Two · England | 3–2 | League Two · England |
| 2016-12-17 | WycombevLeyton OrientLeague Two · England | 1–0 | League Two · England |