| 1 | Tue 12 Aug | 250-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 2 | Sat 30 Aug | 250-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 3 | Tue 2 Sep | 253-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 4 | Sat 6 Sep | 253-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 5 | Sat 20 Sep | 251-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 27 Sep | 252-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 7 | Sat 4 Oct | 253-4 v Cardiff CityCardiff City 4-3 Leyton Orient | Sky Bet League One |
| 8 | Tue 7 Oct | 252-1 v Crawley TownLeyton Orient 2-1 Crawley Town | EFL Trophy Southern Group F |
| 9 | Sat 11 Oct | 254-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 10 | Sat 18 Oct | 250-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 11 | Tue 28 Oct | 251-0 v Aston Villa U21Leyton Orient 1-0 Aston Villa U21 | EFL Trophy Southern Group F |
| 12 | Sat 8 Nov | 251-4 v Wycombe WanderersWycombe Wanderers 4-1 Leyton Orient | Sky Bet League One |
| 13 | Sat 15 Nov | 25 2-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 14 | Sat 22 Nov | 251-1 v BlackpoolLeyton Orient 1-1 Blackpool | Sky Bet League One |
| 15 | Sat 29 Nov | 254-0 v Burton AlbionBurton Albion 0-4 Leyton Orient | Sky Bet League One |
| 16 | Tue 2 Dec | 250-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
| 17 | Fri 5 Dec | 250-4 v Salford CitySalford City 4-0 Leyton Orient | Emirates FA Cup Second Round |
| 18 | Tue 9 Dec | 251-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 19 | Sat 13 Dec | 252-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
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