| 1 | Tue 2 Sep | 323-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 2 | Sat 6 Sep | 323-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 3 | Sat 13 Sep | 321-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 4 | Sat 20 Sep | 321-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 27 Sep | 322-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 6 | Sat 4 Oct | 323-4 v Cardiff CityCardiff City 4-3 Leyton Orient | Sky Bet League One |
| 7 | Tue 7 Oct | 322-1 v Crawley TownLeyton Orient 2-1 Crawley Town | EFL Trophy Southern Group F |
| 8 | Sat 11 Oct | 324-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 9 | Sat 18 Oct | 320-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 10 | Sat 25 Oct | 321-0 v Lincoln CityLeyton Orient 1-0 Lincoln City | Sky Bet League One |
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