| 1 | Tue 17 Sep | 241-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 2 | Sat 19 Oct | 240-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 3 | Tue 22 Oct | 241-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 4 | Sun 3 Nov | 242-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 5 | Sat 9 Nov | 243-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 6 | Sat 23 Nov | 240-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 7 | Tue 26 Nov | 24 0-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 8 | Sat 30 Nov | 242-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 9 | Tue 3 Dec | 243-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 10 | Sat 7 Dec | 242-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 11 | Sat 14 Dec | 240-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 12 | Sat 21 Dec | 244-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 13 | Thu 26 Dec | 243-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 14 | Sun 29 Dec | 24 2-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 15 | Wed 1 Jan | 24 3-2 v Bristol RoversBristol Rovers 2-3 Leyton Orient | Sky Bet League One |
| 16 | Sat 4 Jan | 241-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 17 | Tue 14 Jan | 241-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 18 | Sat 18 Jan | 240-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 19 | Tue 21 Jan | 240-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 20 | Sat 25 Jan | 242-0 v ReadingLeyton Orient 2-0 Reading | Sky Bet League One |
| 21 | Tue 28 Jan | 24 6-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 22 | Sat 1 Feb | 240-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 23 | Sat 8 Feb | 241-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 24 | Tue 11 Feb | 243-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 25 | Sat 15 Feb | 243-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 26 | Tue 18 Feb | 242-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 27 | Sat 22 Feb | 24 1-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 28 | Tue 25 Feb | 240-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 29 | Sat 1 Mar | 241-2 v Charlton AthleticLeyton Orient 1-2 Charlton Athletic | Sky Bet League One |
| 30 | Tue 4 Mar | 240-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 31 | Sat 8 Mar | 241-2 v Northampton TownLeyton Orient 1-2 Northampton Town | Sky Bet League One |
| 32 | Sat 15 Mar | 242-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
| 33 | Thu 27 Mar | 241-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 34 | Tue 1 Apr | 241-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
| 35 | Sat 5 Apr | 240-0 v Wigan AthleticLeyton Orient 0-0 Wigan Athletic | Sky Bet League One |
| 36 | Tue 8 Apr | 243-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League One |
| 37 | Sat 12 Apr | 243-1 v Crawley TownCrawley Town 1-3 Leyton Orient | Sky Bet League One |
| 38 | Fri 18 Apr | 244-3 v BarnsleyLeyton Orient 4-3 Barnsley | Sky Bet League One |
| 39 | Mon 21 Apr | 242-1 v Cambridge UnitedCambridge United 1-2 Leyton Orient | Sky Bet League One |
| 40 | Sat 26 Apr | 241-0 v Wycombe WanderersLeyton Orient 1-0 Wycombe Wanderers | Sky Bet League One |
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