| 1 | Sat 9 Aug | 142-0 v Wigan AthleticLeyton Orient 2-0 Wigan Athletic | Sky Bet League One |
| 2 | Tue 12 Aug | 140-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 3 | Sat 16 Aug | 142-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 4 | Tue 19 Aug | 141-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 23 Aug | 141-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 30 Aug | 140-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 7 | Tue 2 Sep | 143-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 8 | Sat 6 Sep | 143-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 9 | Sat 13 Sep | 141-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 10 | Sat 25 Oct | 141-0 v Lincoln CityLeyton Orient 1-0 Lincoln City | Sky Bet League One |
| 11 | Mon 3 Nov | 141-0 v TamworthTamworth 0-1 Leyton Orient | Emirates FA Cup First Round |
| 12 | Sat 8 Nov | 141-4 v Wycombe WanderersWycombe Wanderers 4-1 Leyton Orient | Sky Bet League One |
| 13 | Sat 15 Nov | 142-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 14 | Sat 22 Nov | 141-1 v BlackpoolLeyton Orient 1-1 Blackpool | Sky Bet League One |
| 15 | Sat 29 Nov | 144-0 v Burton AlbionBurton Albion 0-4 Leyton Orient | Sky Bet League One |
| 16 | Tue 2 Dec | 140-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
| 17 | Fri 5 Dec | 140-4 v Salford CitySalford City 4-0 Leyton Orient | Emirates FA Cup Second Round |
| 18 | Tue 9 Dec | 141-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 19 | Sat 13 Dec | 14 2-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
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