| 1 | Sat 5 Aug | 50-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 2 | Tue 15 Aug | 5 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 3 | Sat 26 Aug | 52-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 4 | Sat 2 Sep | 50-3 v StevenageLeyton Orient 0-3 Stevenage | Sky Bet League One |
| 5 | Sat 23 Sep | 51-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 6 | Sat 30 Sep | 50-1 v Fleetwood TownFleetwood Town 1-0 Leyton Orient | Sky Bet League One |
| 7 | Sat 7 Oct | 52-1 v ReadingLeyton Orient 2-1 Reading | Sky Bet League One |
| 8 | Sat 14 Oct | 51-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League One |
| 9 | Sat 21 Oct | 51-1 v BarnsleyLeyton Orient 1-1 Barnsley | Sky Bet League One |
| 10 | Tue 24 Oct | 5 2-2 v Northampton TownNorthampton Town 2-2 Leyton Orient | Sky Bet League One |
| 11 | Sat 28 Oct | 50-0 v Burton AlbionBurton Albion 0-0 Leyton Orient | Sky Bet League One |
| 12 | Sat 4 Nov | 5 3-1 v Carlisle UnitedLeyton Orient 3-1 Carlisle United | Emirates FA Cup First Round |
| 13 | Tue 7 Nov | 51-2 v PortsmouthLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 14 | Sat 11 Nov | 52-3 v Oxford UnitedLeyton Orient 2-3 Oxford United | Sky Bet League One |
| 15 | Tue 21 Nov | 5 0-1 v Lincoln CityLeyton Orient 0-1 Lincoln City | Sky Bet League One |
| 16 | Sat 25 Nov | 51-1 v Wigan AthleticLeyton Orient 1-1 Wigan Athletic | Sky Bet League One |
| 17 | Tue 28 Nov | 51-1 v Bristol RoversBristol Rovers 1-1 Leyton Orient | Sky Bet League One |
| 18 | Sun 3 Dec | 50-1 v ChesterfieldChesterfield 1-0 Leyton Orient | Emirates FA Cup Second Round |
| 19 | Sat 9 Dec | 50-3 v Derby CountyLeyton Orient 0-3 Derby County | Sky Bet League One |
| 20 | Sat 16 Dec | 52-1 v Cheltenham TownCheltenham Town 1-2 Leyton Orient | Sky Bet League One |
| 21 | Sat 23 Dec | 5 2-3 v Bolton WanderersBolton Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 22 | Tue 26 Dec | 5 1-0 v Charlton AthleticLeyton Orient 1-0 Charlton Athletic | Sky Bet League One |
| 23 | Fri 29 Dec | 50-0 v Wycombe WanderersLeyton Orient 0-0 Wycombe Wanderers | Sky Bet League One |
| 24 | Mon 1 Jan | 52-0 v Cambridge UnitedCambridge United 0-2 Leyton Orient | Sky Bet League One |
| 25 | Sat 13 Jan | 53-0 v PortsmouthPortsmouth 0-3 Leyton Orient | Sky Bet League One |
| 26 | Sat 20 Jan | 51-0 v Bolton WanderersLeyton Orient 1-0 Bolton Wanderers | Sky Bet League One |
| 27 | Sat 27 Jan | 51-1 v ReadingReading 1-1 Leyton Orient | Sky Bet League One |
| 28 | Sat 3 Feb | 53-2 v Carlisle UnitedLeyton Orient 3-2 Carlisle United | Sky Bet League One |
| 29 | Tue 6 Feb | 51-0 v Port ValePort Vale 0-1 Leyton Orient | Sky Bet League One |
| 30 | Sat 10 Feb | 51-2 v BarnsleyBarnsley 2-1 Leyton Orient | Sky Bet League One |
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