| 1 | Sat 8 Aug | 2 2-0 v Oxford UnitedLeyton Orient 2-0 Oxford United | Carabao Cup First Round |
| 2 | Sat 15 Aug | 21-2 v Sheffield WednesdayLeyton Orient 1-2 Sheffield Wednesday | Sky Bet League One |
| 3 | Sat 22 Aug | 22-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 4 | Tue 25 Aug | 20-0 v WalsallWalsall 0-0 Leyton Orient | Carabao Cup Second Round |
| 5 | Sat 29 Aug | 2 1-3 v BarnsleyLeyton Orient 1-3 Barnsley | Sky Bet League One |
| 6 | Tue 1 Sep | 2 5-0 v BromleyBromley 0-5 Leyton Orient | Sky Bet League One |
| 7 | Sat 5 Sep | 21-1 v Luton TownLuton Town 1-1 Leyton Orient | Sky Bet League One |
| 8 | Tue 8 Sep | 21-3 v Bradford CityLeyton Orient 1-3 Bradford City | Carabao Cup Third Round |
| 9 | Sat 12 Sep | 22-3 v Wycombe WanderersLeyton Orient 2-3 Wycombe Wanderers | Sky Bet League One |
| 10 | Tue 15 Sep | 21-2 v Arsenal U21Leyton Orient 1-2 Arsenal U21 | EFL Trophy Southern Group F |
| 11 | Sat 19 Sep | 21-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 12 | Sat 3 Oct | 20-2 v Plymouth ArgyleLeyton Orient 0-2 Plymouth Argyle | Sky Bet League One |
| 13 | Sat 10 Oct | 20-0 v Bradford CityBradford City 0-0 Leyton Orient | Sky Bet League One |
| 14 | Sat 17 Oct | 22-0 v BlackpoolLeyton Orient 2-0 Blackpool | Sky Bet League One |
| 15 | Wed 21 Oct | 20-1 v ReadingReading 1-0 Leyton Orient | Sky Bet League One |
| 16 | Sat 24 Oct | 21-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
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