| 1 | Sat 2 Aug | 40-3 v Huddersfield TownHuddersfield Town 3-0 Leyton Orient | Sky Bet League One |
| 2 | Tue 12 Aug | 40-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 3 | Tue 19 Aug | 41-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 4 | Sat 23 Aug | 41-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 5 | Tue 2 Sep | 4 3-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 6 | Sat 6 Sep | 43-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 7 | Sat 13 Sep | 4 1-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 8 | Sat 20 Sep | 41-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 9 | Sat 27 Sep | 42-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 10 | Tue 7 Oct | 42-1 v Crawley TownLeyton Orient 2-1 Crawley Town | EFL Trophy Southern Group F |
| 11 | Sat 11 Oct | 44-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 12 | Sat 18 Oct | 40-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 13 | Sat 25 Oct | 41-0 v Lincoln CityLeyton Orient 1-0 Lincoln City | Sky Bet League One |
| 14 | Tue 28 Oct | 41-0 v Aston Villa U21Leyton Orient 1-0 Aston Villa U21 | EFL Trophy Southern Group F |
| 15 | Sat 15 Nov | 4 2-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 16 | Sat 29 Nov | 44-0 v Burton AlbionBurton Albion 0-4 Leyton Orient | Sky Bet League One |
| 17 | Tue 2 Dec | 40-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
| 18 | Fri 5 Dec | 40-4 v Salford CitySalford City 4-0 Leyton Orient | Emirates FA Cup Second Round |
| 19 | Tue 9 Dec | 41-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 20 | Sat 13 Dec | 42-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
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