| 1 | Sat 5 Aug | 20-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 2 | Tue 15 Aug | 2 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 3 | Sat 19 Aug | 20-0 v BlackpoolBlackpool 0-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 26 Aug | 2 2-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 5 | Sat 2 Sep | 20-3 v StevenageLeyton Orient 0-3 Stevenage | Sky Bet League One |
| 6 | Tue 5 Sep | 21-2 v GillinghamGillingham 2-1 Leyton Orient | EFL Trophy |
| 7 | Sat 9 Sep | 22-1 v Exeter CityExeter City 1-2 Leyton Orient | Sky Bet League One |
| 8 | Sat 16 Sep | 21-1 v Peterborough UnitedPeterborough United 1-1 Leyton Orient | Sky Bet League One |
| 9 | Sat 23 Sep | 2 1-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 10 | Sat 30 Sep | 20-1 v Fleetwood TownFleetwood Town 1-0 Leyton Orient | Sky Bet League One |
| 11 | Sat 7 Oct | 22-1 v ReadingLeyton Orient 2-1 Reading | Sky Bet League One |
| 12 | Sat 14 Oct | 21-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League One |
| 13 | Tue 24 Oct | 22-2 v Northampton TownNorthampton Town 2-2 Leyton Orient | Sky Bet League One |
| 14 | Sat 28 Oct | 20-0 v Burton AlbionBurton Albion 0-0 Leyton Orient | Sky Bet League One |
| 15 | Sat 4 Nov | 23-1 v Carlisle UnitedLeyton Orient 3-1 Carlisle United | Emirates FA Cup First Round |
| 16 | Tue 7 Nov | 21-2 v PortsmouthLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 17 | Sat 11 Nov | 22-3 v Oxford UnitedLeyton Orient 2-3 Oxford United | Sky Bet League One |
| 18 | Tue 21 Nov | 20-1 v Lincoln CityLeyton Orient 0-1 Lincoln City | Sky Bet League One |
| 19 | Sat 25 Nov | 2 1-1 v Wigan AthleticLeyton Orient 1-1 Wigan Athletic | Sky Bet League One |
| 20 | Tue 28 Nov | 21-1 v Bristol RoversBristol Rovers 1-1 Leyton Orient | Sky Bet League One |
| 21 | Sun 3 Dec | 20-1 v ChesterfieldChesterfield 1-0 Leyton Orient | Emirates FA Cup Second Round |
| 22 | Sat 9 Dec | 20-3 v Derby CountyLeyton Orient 0-3 Derby County | Sky Bet League One |
| 23 | Sat 16 Dec | 22-1 v Cheltenham TownCheltenham Town 1-2 Leyton Orient | Sky Bet League One |
| 24 | Sat 23 Dec | 2 2-3 v Bolton WanderersBolton Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 25 | Tue 26 Dec | 2 1-0 v Charlton AthleticLeyton Orient 1-0 Charlton Athletic | Sky Bet League One |
| 26 | Fri 29 Dec | 20-0 v Wycombe WanderersLeyton Orient 0-0 Wycombe Wanderers | Sky Bet League One |
| 27 | Mon 1 Jan | 2 2-0 v Cambridge UnitedCambridge United 0-2 Leyton Orient | Sky Bet League One |
| 28 | Sat 13 Jan | 23-0 v PortsmouthPortsmouth 0-3 Leyton Orient | Sky Bet League One |
| 29 | Sat 27 Jan | 21-1 v ReadingReading 1-1 Leyton Orient | Sky Bet League One |
| 30 | Sat 3 Feb | 23-2 v Carlisle UnitedLeyton Orient 3-2 Carlisle United | Sky Bet League One |
| 31 | Tue 6 Feb | 21-0 v Port ValePort Vale 0-1 Leyton Orient | Sky Bet League One |
| 32 | Sat 10 Feb | 21-2 v BarnsleyBarnsley 2-1 Leyton Orient | Sky Bet League One |
| 33 | Tue 13 Feb | 24-3 v Northampton TownLeyton Orient 4-3 Northampton Town | Sky Bet League One |
| 34 | Sat 17 Feb | 21-2 v Burton AlbionLeyton Orient 1-2 Burton Albion | Sky Bet League One |
| 35 | Sat 24 Feb | 22-1 v Oxford UnitedOxford United 1-2 Leyton Orient | Sky Bet League One |
| 36 | Tue 27 Feb | 21-0 v BlackpoolLeyton Orient 1-0 Blackpool | Sky Bet League One |
| 37 | Sat 2 Mar | 20-1 v Bristol RoversLeyton Orient 0-1 Bristol Rovers | Sky Bet League One |
| 38 | Sat 9 Mar | 20-1 v Wigan AthleticWigan Athletic 1-0 Leyton Orient | Sky Bet League One |
| 39 | Tue 12 Mar | 20-0 v Port ValeLeyton Orient 0-0 Port Vale | Sky Bet League One |
| 40 | Sat 16 Mar | 21-0 v StevenageStevenage 0-1 Leyton Orient | Sky Bet League One |
| 41 | Fri 29 Mar | 20-1 v Lincoln CityLincoln City 1-0 Leyton Orient | Sky Bet League One |
| 42 | Mon 1 Apr | 21-2 v Peterborough UnitedLeyton Orient 1-2 Peterborough United | Sky Bet League One |
| 43 | Sat 6 Apr | 23-1 v Cheltenham TownLeyton Orient 3-1 Cheltenham Town | Sky Bet League One |
| 44 | Tue 9 Apr | 22-2 v Exeter CityLeyton Orient 2-2 Exeter City | Sky Bet League One |
| 45 | Sat 13 Apr | 20-3 v Derby CountyDerby County 3-0 Leyton Orient | Sky Bet League One |
| 46 | Sat 20 Apr | 20-1 v Fleetwood TownLeyton Orient 0-1 Fleetwood Town | Sky Bet League One |
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