| 1 | Sat 10 Aug | 11-2 v Bolton WanderersLeyton Orient 1-2 Bolton Wanderers | Sky Bet League One |
| 2 | Tue 13 Aug | 14-1 v Newport CountyLeyton Orient 4-1 Newport County | Carabao Cup First Round |
| 3 | Sat 17 Aug | 10-1 v Charlton AthleticCharlton Athletic 1-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 24 Aug | 11-2 v Birmingham CityLeyton Orient 1-2 Birmingham City | Sky Bet League One |
| 5 | Tue 27 Aug | 11-0 v MillwallMillwall 0-1 Leyton Orient | Carabao Cup Second Round |
| 6 | Sat 31 Aug | 10-3 v Shrewsbury TownShrewsbury Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Sat 14 Sep | 1 1-0 v ReadingReading 0-1 Leyton Orient | Sky Bet League One |
| 8 | Sat 21 Sep | 14-1 v Stockport CountyStockport County 1-4 Leyton Orient | Sky Bet League One |
| 9 | Tue 24 Sep | 12-2 v Peterborough UnitedLeyton Orient 2-2 Peterborough United | Sky Bet League One |
| 10 | Sat 28 Sep | 10-0 v WrexhamLeyton Orient 0-0 Wrexham | Sky Bet League One |
| 11 | Tue 1 Oct | 10-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League One |
| 12 | Sat 5 Oct | 11-2 v Lincoln CityLincoln City 2-1 Leyton Orient | Sky Bet League One |
| 13 | Tue 8 Oct | 11-1 v Colchester UnitedLeyton Orient 1-1 Colchester United | EFL Trophy Southern Group E |
| 14 | Tue 12 Nov | 13-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | EFL Trophy Southern Group E |
| 15 | Tue 10 Dec | 12-0 v Charlton AthleticCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
Football Web Pages