| 1 | Sat 10 Aug | 21-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 24-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 2 0-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Tue 27 Aug | 21-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 5 | Sat 14 Sep | 2 1-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 6 | Tue 17 Sep | 21-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 7 | Sat 21 Sep | 2 4-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 8 | Tue 24 Sep | 22-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 9 | Sat 28 Sep | 20-0 v WrexhamLeyton Orient 0-0 Wrexham | Sky Bet League One |
| 10 | Sat 5 Oct | 21-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 11 | Sat 19 Oct | 2 0-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 12 | Tue 22 Oct | 2 1-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 13 | Sat 9 Nov | 2 3-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 14 | Tue 12 Nov | 2 3-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 15 | Sat 23 Nov | 20-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 16 | Tue 26 Nov | 20-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
| 17 | Sat 30 Nov | 22-1 v Oldham AthleticLeyton Orient 2-1 Oldham Athletic | Emirates FA Cup Second Round |
| 18 | Tue 3 Dec | 23-0 v Bristol RoversLeyton Orient 3-0 Bristol Rovers | Sky Bet League One |
| 19 | Sat 7 Dec | 22-0 v Wigan AthleticWigan Athletic 0-2 Leyton Orient | Sky Bet League One |
| 20 | Sat 14 Dec | 20-0 v Burton AlbionLeyton Orient 0-0 Burton Albion | Sky Bet League One |
| 21 | Tue 14 Jan | 21-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 22 | Sat 18 Jan | 20-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 23 | Tue 21 Jan | 20-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 24 | Sat 25 Jan | 22-0 v ReadingLeyton Orient 2-0 Reading | Sky Bet League One |
| 25 | Tue 28 Jan | 26-2 v Exeter CityExeter City 2-6 Leyton Orient | Sky Bet League One |
| 26 | Sat 1 Feb | 20-1 v Stockport CountyLeyton Orient 0-1 Stockport County | Sky Bet League One |
| 27 | Sat 8 Feb | 21-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 28 | Tue 11 Feb | 23-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 29 | Sat 15 Feb | 23-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 30 | Sat 5 Apr | 2 0-0 v Wigan AthleticLeyton Orient 0-0 Wigan Athletic | Sky Bet League One |
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