| 1 | Sat 2 Aug | 210-3 v Huddersfield TownHuddersfield Town 3-0 Leyton Orient | Sky Bet League One |
| 2 | Sat 9 Aug | 212-0 v Wigan AthleticLeyton Orient 2-0 Wigan Athletic | Sky Bet League One |
| 3 | Tue 12 Aug | 21 0-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 4 | Sat 16 Aug | 212-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 5 | Sat 23 Aug | 211-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 30 Aug | 210-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 7 | Tue 2 Sep | 213-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 8 | Sat 6 Sep | 213-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 9 | Sat 13 Sep | 211-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 20 Sep | 211-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 11 | Sat 27 Sep | 212-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 12 | Tue 28 Oct | 211-0 v Aston Villa U21Leyton Orient 1-0 Aston Villa U21 | EFL Trophy Southern Group F |
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