| 1 | Sat 8 Aug | 12-0 v Oxford UnitedLeyton Orient 2-0 Oxford United | Carabao Cup First Round |
| 2 | Sat 15 Aug | 11-2 v Sheffield WednesdayLeyton Orient 1-2 Sheffield Wednesday | Sky Bet League One |
| 3 | Sat 22 Aug | 12-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 4 | Sat 5 Sep | 11-1 v Luton TownLuton Town 1-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 12 Sep | 12-3 v Wycombe WanderersLeyton Orient 2-3 Wycombe Wanderers | Sky Bet League One |
| 6 | Sat 19 Sep | 11-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 7 | Sat 3 Oct | 10-2 v Plymouth ArgyleLeyton Orient 0-2 Plymouth Argyle | Sky Bet League One |
| 8 | Sat 10 Oct | 10-0 v Bradford CityBradford City 0-0 Leyton Orient | Sky Bet League One |
| 9 | Sat 17 Oct | 12-0 v BlackpoolLeyton Orient 2-0 Blackpool | Sky Bet League One |
| 10 | Wed 21 Oct | 10-1 v ReadingReading 1-0 Leyton Orient | Sky Bet League One |
| 11 | Sat 24 Oct | 11-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
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