| 1 | Sat 2 Aug | 20-3 v Huddersfield TownHuddersfield Town 3-0 Leyton Orient | Sky Bet League One |
| 2 | Sat 9 Aug | 22-0 v Wigan AthleticLeyton Orient 2-0 Wigan Athletic | Sky Bet League One |
| 3 | Sat 16 Aug | 22-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 4 | Tue 19 Aug | 21-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 23 Aug | 21-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 30 Aug | 2 0-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 7 | Tue 2 Sep | 23-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 8 | Sat 6 Sep | 23-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 9 | Sat 13 Sep | 2 1-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 20 Sep | 2 1-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 11 | Sat 27 Sep | 22-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 12 | Sat 11 Oct | 24-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 13 | Sat 18 Oct | 20-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 14 | Sat 25 Oct | 21-0 v Lincoln CityLeyton Orient 1-0 Lincoln City | Sky Bet League One |
| 15 | Mon 3 Nov | 21-0 v TamworthTamworth 0-1 Leyton Orient | Emirates FA Cup First Round |
| 16 | Sat 8 Nov | 2 1-4 v Wycombe WanderersWycombe Wanderers 4-1 Leyton Orient | Sky Bet League One |
| 17 | Sat 13 Dec | 22-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
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