| 1 | Sat 10 Aug | 31-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 34-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 3 0-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 31-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 3 1-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 3 0-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Tue 17 Sep | 31-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 8 | Tue 8 Oct | 31-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 9 | Tue 22 Oct | 31-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 10 | Sun 3 Nov | 3 2-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 11 | Tue 12 Nov | 33-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 12 | Sat 30 Nov | 32-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 13 | Tue 3 Dec | 33-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 14 | Sat 7 Dec | 32-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 15 | Sat 14 Dec | 30-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 16 | Sun 29 Dec | 32-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 17 | Sat 4 Jan | 31-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 18 | Tue 14 Jan | 31-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 19 | Sat 18 Jan | 30-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 20 | Tue 21 Jan | 30-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 21 | Sat 25 Jan | 32-0 v ReadingLeyton Orient 2-0 Reading | Sky Bet League One |
| 22 | Tue 28 Jan | 36-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 23 | Tue 18 Feb | 3 2-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 24 | Sat 22 Feb | 31-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 25 | Tue 25 Feb | 30-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 26 | Sat 1 Mar | 31-2 v Charlton AthleticLeyton Orient 1-2 Charlton Athletic | Sky Bet League One |
| 27 | Tue 4 Mar | 30-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 28 | Sat 8 Mar | 31-2 v Northampton TownLeyton Orient 1-2 Northampton Town | Sky Bet League One |
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