| 1 | Sat 29 Nov | 114-0 v Burton AlbionBurton Albion 0-4 Leyton Orient | Sky Bet League One |
| 2 | Tue 2 Dec | 440-1 v Plymouth ArgyleLeyton Orient 0-1 Plymouth Argyle | EFL Trophy Round of 32 |
| 3 | Tue 9 Dec | 441-1 v Luton TownLeyton Orient 1-1 Luton Town | Sky Bet League One |
| 4 | Sat 13 Dec | 442-3 v BarnsleyBarnsley 3-2 Leyton Orient | Sky Bet League One |
| 5 | Sat 20 Dec | 442-1 v Bradford CityLeyton Orient 2-1 Bradford City | Sky Bet League One |
| 6 | Mon 29 Dec | 440-3 v Luton TownLuton Town 3-0 Leyton Orient | Sky Bet League One |
| 7 | Thu 1 Jan | 441-3 v AFC WimbledonLeyton Orient 1-3 AFC Wimbledon | Sky Bet League One |
| 8 | Sat 10 Jan | 44 1-1 v Cardiff CityLeyton Orient 1-1 Cardiff City | Sky Bet League One |
| 9 | Sat 17 Jan | 44 3-1 v ReadingLeyton Orient 3-1 Reading | Sky Bet League One |
| 10 | Sat 24 Jan | 441-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 11 | Tue 27 Jan | 440-3 v Doncaster RoversDoncaster Rovers 3-0 Leyton Orient | Sky Bet League One |
| 12 | Sat 31 Jan | 440-1 v Port ValeLeyton Orient 0-1 Port Vale | Sky Bet League One |
| 13 | Sat 7 Feb | 440-0 v Stockport CountyStockport County 0-0 Leyton Orient | Sky Bet League One |
| 14 | Tue 17 Feb | 44 1-3 v Plymouth ArgyleLeyton Orient 1-3 Plymouth Argyle | Sky Bet League One |
| 15 | Sat 21 Feb | 442-1 v Northampton TownNorthampton Town 1-2 Leyton Orient | Sky Bet League One |
| 16 | Sat 28 Feb | 441-3 v BarnsleyLeyton Orient 1-3 Barnsley | Sky Bet League One |
| 17 | Sat 7 Mar | 441-2 v Bradford CityBradford City 2-1 Leyton Orient | Sky Bet League One |
| 18 | Tue 10 Mar | 44 2-1 v StevenageStevenage 1-2 Leyton Orient | Sky Bet League One |
| 19 | Sat 14 Mar | 44 2-1 v Peterborough UnitedLeyton Orient 2-1 Peterborough United | Sky Bet League One |
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