| 1 | Sat 2 Aug | 10-3 v Huddersfield TownHuddersfield Town 3-0 Leyton Orient | Sky Bet League One |
| 2 | Sat 9 Aug | 12-0 v Wigan AthleticLeyton Orient 2-0 Wigan Athletic | Sky Bet League One |
| 3 | Tue 12 Aug | 10-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 4 | Sat 16 Aug | 12-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 5 | Tue 19 Aug | 1 1-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 23 Aug | 11-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 7 | Sat 30 Aug | 10-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 8 | Sat 13 Sep | 11-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 9 | Sat 20 Sep | 11-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 10 | Sat 27 Sep | 12-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 11 | Sat 4 Oct | 13-4 v Cardiff CityCardiff City 4-3 Leyton Orient | Sky Bet League One |
| 12 | Tue 28 Oct | 11-0 v Aston Villa U21Leyton Orient 1-0 Aston Villa U21 | EFL Trophy Southern Group F |
| 13 | Tue 2 Dec | 10-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
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