| 1 | Tue 13 Aug | 16 4-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 2 | Sat 17 Aug | 160-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 3 | Tue 27 Aug | 161-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 4 | Tue 17 Sep | 161-3 v BrentfordBrentford 3-1 Leyton Orient | Carabao Cup Third Round |
| 5 | Sat 21 Sep | 164-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 6 | Tue 24 Sep | 162-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 7 | Tue 1 Oct | 160-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 8 | Tue 8 Oct | 161-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 9 | Sat 9 Nov | 163-0 v BlackpoolLeyton Orient 3-0 Blackpool | Sky Bet League One |
| 10 | Tue 12 Nov | 163-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 11 | Sat 23 Nov | 16 0-0 v StevenageStevenage 0-0 Leyton Orient | Sky Bet League One |
| 12 | Tue 26 Nov | 160-2 v Huddersfield TownLeyton Orient 0-2 Huddersfield Town | Sky Bet League One |
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