| 1 | Sat 10 Aug | 211-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 214-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 210-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 21 1-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 21 1-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 210-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Sat 14 Sep | 21 1-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 8 | Sat 21 Sep | 21 4-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 9 | Tue 24 Sep | 212-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 10 | Tue 1 Oct | 210-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 11 | Sat 5 Oct | 211-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 12 | Tue 8 Oct | 211-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 13 | Sat 19 Oct | 210-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 14 | Tue 22 Oct | 211-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 15 | Sun 3 Nov | 212-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 16 | Sat 9 Nov | 213-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 17 | Tue 12 Nov | 213-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 18 | Sat 23 Nov | 21 0-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 19 | Sat 30 Nov | 212-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 20 | Tue 3 Dec | 213-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 21 | Sat 7 Dec | 212-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 22 | Tue 10 Dec | 212-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 23 | Sat 14 Dec | 210-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 24 | Sat 21 Dec | 21 4-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 25 | Thu 26 Dec | 21 3-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 26 | Sun 29 Dec | 212-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 27 | Wed 1 Jan | 213-2 v Bristol RoversBristol Rovers 2-3 Leyton Orient | Sky Bet League One |
| 28 | Sat 4 Jan | 211-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 29 | Thu 27 Mar | 211-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 30 | Tue 1 Apr | 211-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
| 31 | Mon 21 Apr | 212-1 v Cambridge UnitedCambridge United 1-2 Leyton Orient | Sky Bet League One |
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