| 2019-04-27 | Leyton OrientvBraintree TownNational League · England | 0–0 | National League · England |
| 2019-04-22 | SolihullvLeyton OrientNational League · England | 0–0 | National League · England |
| 2019-04-19 | Leyton OrientvHarrogateNational League · England | 2–0 | National League · England |
| 2019-04-13 | SuttonvLeyton OrientNational League · England | 1–2 | National League · England |
| 2019-04-09 | Leyton OrientvEastleighNational League · England | 3–2 | National League · England |
| 2019-04-06 | Leyton OrientvHalifaxNational League · England | 2–2 | National League · England |
| 2019-04-02 | BromleyvLeyton OrientNational League · England | 2–1 | National League · England |
| 2019-03-30 | BarnetvLeyton OrientNational League · England | 0–0 | National League · England |
| 2019-03-26 | Leyton OrientvFyldeNational League · England | 2–0 | National League · England |
| 2019-03-12 | AldershotvLeyton OrientNational League · England | 1–2 | National League · England |
| 2019-03-09 | Leyton OrientvWrexhamNational League · England | 1–0 | National League · England |
| 2019-03-05 | BarrowvLeyton OrientNational League · England | 2–3 | National League · England |
| 2019-03-02 | Havant & WaterloovillevLeyton OrientNational League · England | 1–2 | National League · England |
| 2019-02-16 | Leyton OrientvMaidenheadNational League · England | 0–1 | National League · England |
| 2019-02-09 | HartlepoolvLeyton OrientNational League · England | 1–1 | National League · England |
| 2019-01-26 | Leyton OrientvMaidstoneNational League · England | 3–0 | National League · England |
| 2019-01-19 | EbbsfleetvLeyton OrientNational League · England | 2–0 | National League · England |
| 2019-01-05 | Leyton OrientvSalfordNational League · England | 0–3 | National League · England |
| 2019-01-01 | Leyton OrientvDag and RedNational League · England | 1–0 | National League · England |