| 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 |
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