| 1 | Sat 10 Aug | 51-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Sat 17 Aug | 50-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 3 | Sat 24 Aug | 51-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 4 | Sat 31 Aug | 50-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 5 | Sat 14 Sep | 5 1-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 6 | Sat 21 Sep | 54-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 7 | Tue 24 Sep | 52-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 8 | Sat 19 Oct | 50-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 9 | Tue 22 Oct | 51-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 10 | Sun 3 Nov | 52-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 11 | Sat 9 Nov | 53-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 12 | Tue 12 Nov | 5 3-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 13 | Sat 23 Nov | 50-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 14 | Tue 26 Nov | 50-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 15 | Tue 3 Dec | 53-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 16 | Sat 7 Dec | 52-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 17 | Sat 14 Dec | 50-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 18 | Sat 21 Dec | 54-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 19 | Thu 26 Dec | 53-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 20 | Wed 1 Jan | 5 3-2 v Bristol RoversBristol Rovers 2-3 Leyton Orient | Sky Bet League One |
| 21 | Tue 28 Jan | 56-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 22 | Sat 1 Feb | 50-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 23 | Sat 8 Feb | 51-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 24 | Tue 11 Feb | 53-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 25 | Tue 18 Feb | 52-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 26 | Tue 1 Apr | 51-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
| 27 | Sat 5 Apr | 50-0 v Wigan AthleticLeyton Orient 0-0 Wigan Athletic | Sky Bet League One |
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