| 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 |
| 11 | Mon 3 Nov | 321-0 v TamworthTamworth 0-1 Leyton Orient | Emirates FA Cup First Round |
| 12 | Sat 8 Nov | 321-4 v Wycombe WanderersWycombe Wanderers 4-1 Leyton Orient | Sky Bet League One |
| 13 | Sat 15 Nov | 322-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 14 | Sat 22 Nov | 321-1 v BlackpoolLeyton Orient 1-1 Blackpool | Sky Bet League One |
| 15 | Sat 29 Nov | 324-0 v Burton AlbionBurton Albion 0-4 Leyton Orient | Sky Bet League One |
| 16 | Fri 5 Dec | 320-4 v Salford CitySalford City 4-0 Leyton Orient | Emirates FA Cup Second Round |
| 17 | Tue 9 Dec | 321-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 18 | Sat 13 Dec | 322-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
| 19 | Sat 20 Dec | 322-1 v Bradford CityLeyton Orient 2-1 Bradford City | Sky Bet League One |
| 20 | Fri 26 Dec | 320-1 v Peterborough UnitedPeterborough United 1-0 Leyton Orient | Sky Bet League One |
| 21 | Mon 29 Dec | 320-3 v Luton TownLuton Town 3-0 Leyton Orient | Sky Bet League One |
| 22 | Thu 1 Jan | 321-3 v AFC WimbledonLeyton Orient 1-3 AFC Wimbledon | Sky Bet League One |
| 23 | Sat 10 Jan | 321-1 v Cardiff CityLeyton Orient 1-1 Cardiff City | Sky Bet League One |
| 24 | Sat 17 Jan | 323-1 v ReadingLeyton Orient 3-1 Reading | Sky Bet League One |
| 25 | Sat 24 Jan | 321-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 26 | Tue 27 Jan | 320-3 v Doncaster RoversDoncaster Rovers 3-0 Leyton Orient | Sky Bet League One |
| 27 | Sat 31 Jan | 32 0-1 v Port ValeLeyton Orient 0-1 Port Vale | Sky Bet League One |
| 28 | Sat 7 Feb | 320-0 v Stockport CountyStockport County 0-0 Leyton Orient | Sky Bet League One |
| 29 | Tue 17 Feb | 321-3 v Plymouth ArgyleLeyton Orient 1-3 Plymouth Argyle | Sky Bet League One |
| 30 | Sat 21 Feb | 322-1 v Northampton TownNorthampton Town 1-2 Leyton Orient | Sky Bet League One |
| 31 | Sat 28 Feb | 321-3 v BarnsleyLeyton Orient 1-3 Barnsley | Sky Bet League One |
| 32 | Sat 7 Mar | 321-2 v Bradford CityBradford City 2-1 Leyton Orient | Sky Bet League One |
| 33 | Tue 10 Mar | 322-1 v StevenageStevenage 1-2 Leyton Orient | Sky Bet League One |
| 34 | Sat 14 Mar | 322-1 v Peterborough UnitedLeyton Orient 2-1 Peterborough United | Sky Bet League One |
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