| 1 | Sat 10 Aug | 201-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 204-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 200-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 201-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 201-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 200-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Sat 14 Sep | 201-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 8 | Tue 17 Sep | 201-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 9 | Tue 1 Oct | 200-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 10 | Tue 8 Oct | 201-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 11 | Sun 3 Nov | 202-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 12 | Sat 9 Nov | 20 3-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 13 | Tue 12 Nov | 203-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 14 | Sat 23 Nov | 200-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 15 | Tue 26 Nov | 200-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 16 | Sat 30 Nov | 202-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 17 | Tue 3 Dec | 203-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 18 | Sat 7 Dec | 202-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 19 | Tue 10 Dec | 202-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 20 | Sat 14 Dec | 200-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 21 | Sat 21 Dec | 204-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 22 | Thu 26 Dec | 203-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 23 | Sun 29 Dec | 202-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 24 | Wed 1 Jan | 203-2 v Bristol RoversBristol Rovers 2-3 Leyton Orient | Sky Bet League One |
| 25 | Sat 4 Jan | 201-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 26 | Tue 14 Jan | 201-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 27 | Tue 21 Jan | 200-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 28 | Sat 1 Feb | 200-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 29 | Sat 8 Feb | 201-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 30 | Tue 11 Feb | 203-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 31 | Sat 15 Feb | 203-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 32 | Tue 18 Feb | 202-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 33 | Sat 22 Feb | 201-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 34 | Tue 25 Feb | 200-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 35 | Sat 1 Mar | 201-2 v Charlton AthleticLeyton Orient 1-2 Charlton Athletic | Sky Bet League One |
| 36 | Tue 4 Mar | 200-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 37 | Sat 8 Mar | 201-2 v Northampton TownLeyton Orient 1-2 Northampton Town | Sky Bet League One |
| 38 | Sat 15 Mar | 202-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
| 39 | Thu 27 Mar | 201-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 40 | Tue 1 Apr | 201-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
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