| 1 | Tue 18 Aug | 61-1 v AFC WimbledonLeyton Orient 1-1 AFC Wimbledon | EFL Trophy Southern Group F |
| 2 | Tue 25 Aug | 60-0 v WalsallWalsall 0-0 Leyton Orient | Carabao Cup Second Round |
| 3 | Tue 1 Sep | 65-0 v BromleyBromley 0-5 Leyton Orient | Sky Bet League One |
| 4 | Sat 5 Sep | 61-1 v Luton TownLuton Town 1-1 Leyton Orient | Sky Bet League One |
| 5 | Tue 8 Sep | 61-3 v Bradford CityLeyton Orient 1-3 Bradford City | Carabao Cup Third Round |
| 6 | Sat 12 Sep | 62-3 v Wycombe WanderersLeyton Orient 2-3 Wycombe Wanderers | Sky Bet League One |
| 7 | Tue 15 Sep | 61-2 v Arsenal U21Leyton Orient 1-2 Arsenal U21 | EFL Trophy Southern Group F |
| 8 | Sat 19 Sep | 61-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 9 | Sat 3 Oct | 60-2 v Plymouth ArgyleLeyton Orient 0-2 Plymouth Argyle | Sky Bet League One |
| 10 | Sat 10 Oct | 60-0 v Bradford CityBradford City 0-0 Leyton Orient | Sky Bet League One |
| 11 | Sat 17 Oct | 62-0 v BlackpoolLeyton Orient 2-0 Blackpool | Sky Bet League One |
| 12 | Wed 21 Oct | 60-1 v ReadingReading 1-0 Leyton Orient | Sky Bet League One |
| 13 | Sat 24 Oct | 61-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
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