| 1 | Sat 14 Sep | 121-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 2 | Sat 21 Sep | 124-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 3 | Tue 24 Sep | 122-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 4 | Sat 28 Sep | 120-0 v WrexhamLeyton Orient 0-0 Wrexham | Sky Bet League One |
| 5 | Tue 1 Oct | 120-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 6 | Sat 5 Oct | 121-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 7 | Sat 19 Oct | 120-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 8 | Tue 22 Oct | 121-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 9 | Sat 9 Nov | 12 3-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 10 | Tue 12 Nov | 123-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 11 | Sat 23 Nov | 120-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 12 | Tue 26 Nov | 120-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 13 | Tue 3 Dec | 12 3-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 14 | Tue 10 Dec | 122-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 15 | Sat 14 Dec | 120-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 16 | Sat 21 Dec | 12 4-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 17 | Thu 26 Dec | 123-0 v Crawley TownLeyton Orient 3-0 Crawley Town | Sky Bet League One |
| 18 | Sun 29 Dec | 122-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 19 | Wed 1 Jan | 123-2 v Bristol RoversBristol Rovers 2-3 Leyton Orient | Sky Bet League One |
| 20 | Sat 4 Jan | 121-0 v Shrewsbury TownLeyton Orient 1-0 Shrewsbury Town | Sky Bet League One |
| 21 | Tue 14 Jan | 121-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 22 | Sat 18 Jan | 120-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 23 | Tue 21 Jan | 120-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 24 | Sat 25 Jan | 122-0 v ReadingLeyton Orient 2-0 Reading | Sky Bet League One |
| 25 | Tue 28 Jan | 126-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 26 | Sat 1 Feb | 120-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 27 | Sat 8 Feb | 121-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 28 | Tue 11 Feb | 123-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 29 | Sat 15 Feb | 123-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 30 | Sat 22 Feb | 121-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 31 | Tue 25 Feb | 12 0-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 32 | Sat 15 Mar | 122-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
| 33 | Thu 27 Mar | 121-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 34 | Tue 1 Apr | 121-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
| 35 | Sat 5 Apr | 120-0 v Wigan AthleticLeyton Orient 0-0 Wigan Athletic | Sky Bet League One |
| 36 | Tue 8 Apr | 123-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League One |
| 37 | Sat 12 Apr | 123-1 v Crawley TownCrawley Town 1-3 Leyton Orient | Sky Bet League One |
| 38 | Fri 18 Apr | 124-3 v BarnsleyLeyton Orient 4-3 Barnsley | Sky Bet League One |
| 39 | Mon 21 Apr | 122-1 v Cambridge UnitedCambridge United 1-2 Leyton Orient | Sky Bet League One |
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