| 1 | Sat 10 Aug | 291-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 294-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 290-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 29 1-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 291-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Tue 17 Sep | 291-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 7 | Tue 8 Oct | 291-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 8 | Sat 19 Oct | 290-1 v Northampton TownNorthampton Town 1-0 Leyton Orient | Sky Bet League One |
| 9 | Sun 3 Nov | 292-2 v Boreham WoodBoreham Wood 2-2 Leyton Orient | Emirates FA Cup First Round |
| 10 | Sat 9 Nov | 293-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 11 | Tue 12 Nov | 29 3-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 12 | Tue 10 Dec | 292-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 13 | Sat 21 Dec | 294-0 v BarnsleyBarnsley 0-4 Leyton Orient | Sky Bet League One |
| 14 | Tue 14 Jan | 291-1 v Derby CountyLeyton Orient 1-1 Derby County | Emirates FA Cup Third Round |
| 15 | Sat 18 Jan | 29 0-0 v Peterborough UnitedPeterborough United 0-0 Leyton Orient | Sky Bet League One |
| 16 | Tue 21 Jan | 290-1 v StevenageLeyton Orient 0-1 Stevenage | EFL Trophy Third Round |
| 17 | Sat 8 Feb | 29 1-2 v Manchester CityLeyton Orient 1-2 Manchester City | Emirates FA Cup Fourth Round |
| 18 | Sat 22 Feb | 291-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
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