| 1 | Sat 10 Aug | 61-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 64-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 60-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 61-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 61-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 60-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Tue 17 Sep | 61-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 8 | Sat 21 Sep | 64-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 9 | Tue 24 Sep | 6 2-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 10 | Sat 28 Sep | 60-0 v WrexhamLeyton Orient 0-0 Wrexham | Sky Bet League One |
| 11 | Tue 1 Oct | 60-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 12 | Sat 5 Oct | 61-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 13 | Tue 8 Oct | 61-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 14 | Sun 3 Nov | 62-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 15 | Tue 12 Nov | 6 3-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 16 | Tue 26 Nov | 60-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 17 | Sat 30 Nov | 62-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 18 | Tue 10 Dec | 62-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 19 | Sat 21 Dec | 64-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 20 | Tue 14 Jan | 61-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 21 | Sat 18 Jan | 6 0-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 22 | Tue 21 Jan | 60-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 23 | Sat 25 Jan | 62-0 v ReadingLeyton Orient 2-0 Reading | Sky Bet League One |
| 24 | Tue 28 Jan | 6 6-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 25 | Sat 1 Feb | 6 0-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 26 | Sat 8 Feb | 6 1-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 27 | Sat 15 Feb | 63-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 28 | Sat 22 Feb | 61-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 29 | Tue 25 Feb | 60-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 30 | Sat 1 Mar | 61-2 v Charlton AthleticLeyton Orient 1-2 Charlton Athletic | Sky Bet League One |
| 31 | Tue 4 Mar | 60-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 32 | Sat 15 Mar | 62-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
| 33 | Thu 27 Mar | 61-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 34 | Sat 5 Apr | 60-0 v Wigan AthleticLeyton Orient 0-0 Wigan Athletic | Sky Bet League One |
| 35 | Tue 8 Apr | 63-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League One |
| 36 | Sat 12 Apr | 63-1 v Crawley TownCrawley Town 1-3 Leyton Orient | Sky Bet League One |
| 37 | Fri 18 Apr | 64-3 v BarnsleyLeyton Orient 4-3 Barnsley | Sky Bet League One |
| 38 | Mon 21 Apr | 62-1 v Cambridge UnitedCambridge United 1-2 Leyton Orient | Sky Bet League One |
| 39 | Sat 26 Apr | 61-0 v Wycombe WanderersLeyton Orient 1-0 Wycombe Wanderers | Sky Bet League One |
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