| 1 | Sat 14 Sep | 41-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 2 | Tue 17 Sep | 4 1-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 3 | Sat 28 Sep | 40-0 v WrexhamLeyton Orient 0-0 Wrexham | Sky Bet League One |
| 4 | Tue 1 Oct | 40-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 5 | Sat 5 Oct | 4 1-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 6 | Tue 8 Oct | 4 1-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 7 | Sat 19 Oct | 40-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 8 | Sun 3 Nov | 42-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 9 | Sat 9 Nov | 43-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 10 | Tue 26 Nov | 40-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 11 | Sat 30 Nov | 42-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 12 | Tue 3 Dec | 43-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 13 | Tue 10 Dec | 42-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 14 | Sat 21 Dec | 44-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 15 | Thu 26 Dec | 43-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 16 | Sun 29 Dec | 42-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 17 | Sat 4 Jan | 41-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 18 | Tue 14 Jan | 41-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 19 | Sat 18 Jan | 40-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 20 | Tue 21 Jan | 40-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 21 | Sat 8 Feb | 41-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 22 | Sat 15 Feb | 43-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 23 | Tue 18 Feb | 42-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 24 | Sat 8 Mar | 4 1-2 v Northampton TownLeyton Orient 1-2 Northampton Town | Sky Bet League One |
| 25 | Sat 15 Mar | 42-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
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