| 1 | Sat 2 Aug | 30-3 v Huddersfield TownHuddersfield Town 3-0 Leyton Orient | Sky Bet League One |
| 2 | Sat 9 Aug | 32-0 v Wigan AthleticLeyton Orient 2-0 Wigan Athletic | Sky Bet League One |
| 3 | Tue 12 Aug | 30-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 4 | Sat 16 Aug | 32-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 5 | Tue 19 Aug | 31-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 23 Aug | 31-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 7 | Sat 30 Aug | 3 0-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 8 | Sat 4 Oct | 33-4 v Cardiff CityCardiff City 4-3 Leyton Orient | Sky Bet League One |
| 9 | Tue 7 Oct | 32-1 v Crawley TownLeyton Orient 2-1 Crawley Town | EFL Trophy Southern Group F |
| 10 | Sat 11 Oct | 34-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 11 | Sat 18 Oct | 30-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 12 | Sat 15 Nov | 32-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 13 | Sat 22 Nov | 3 1-1 v BlackpoolLeyton Orient 1-1 Blackpool | Sky Bet League One |
| 14 | Tue 2 Dec | 30-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
| 15 | Fri 5 Dec | 30-4 v Salford CitySalford City 4-0 Leyton Orient | Emirates FA Cup Second Round |
| 16 | Tue 9 Dec | 31-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 17 | Sat 13 Dec | 32-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
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