| 1 | Tue 12 Aug | 110-1 v Wycombe WanderersLeyton Orient 0-1 Wycombe Wanderers | Carabao Cup First Round |
| 2 | Sat 16 Aug | 112-2 v Stockport CountyLeyton Orient 2-2 Stockport County | Sky Bet League One |
| 3 | Tue 19 Aug | 111-0 v Plymouth ArgylePlymouth Argyle 0-1 Leyton Orient | Sky Bet League One |
| 4 | Sat 23 Aug | 111-4 v Mansfield TownMansfield Town 4-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 30 Aug | 110-1 v Northampton TownLeyton Orient 0-1 Northampton Town | Sky Bet League One |
| 6 | Tue 2 Sep | 11 3-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | EFL Trophy Southern Group F |
| 7 | Sat 6 Sep | 113-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League One |
| 8 | Sat 13 Sep | 11 1-1 v Bolton WanderersLeyton Orient 1-1 Bolton Wanderers | Sky Bet League One |
| 9 | Sat 20 Sep | 111-2 v ReadingReading 2-1 Leyton Orient | Sky Bet League One |
| 10 | Sat 27 Sep | 112-3 v StevenageLeyton Orient 2-3 Stevenage | Sky Bet League One |
| 11 | Sat 4 Oct | 113-4 v Cardiff CityCardiff City 4-3 Leyton Orient | Sky Bet League One |
| 12 | Tue 7 Oct | 112-1 v Crawley TownLeyton Orient 2-1 Crawley Town | EFL Trophy Southern Group F |
| 13 | Sat 11 Oct | 114-0 v Doncaster RoversLeyton Orient 4-0 Doncaster Rovers | Sky Bet League One |
| 14 | Tue 28 Oct | 111-0 v Aston Villa U21Leyton Orient 1-0 Aston Villa U21 | EFL Trophy Southern Group F |
| 15 | Sat 15 Nov | 112-1 v Exeter CityLeyton Orient 2-1 Exeter City | Sky Bet League One |
| 16 | Sat 20 Dec | 112-1 v Bradford CityLeyton Orient 2-1 Bradford City | Sky Bet League One |
| 17 | Fri 26 Dec | 11 0-1 v Peterborough UnitedPeterborough United 1-0 Leyton Orient | Sky Bet League One |
| 18 | Mon 29 Dec | 110-3 v Luton TownLuton Town 3-0 Leyton Orient | Sky Bet League One |
| 19 | Thu 1 Jan | 111-3 v AFC WimbledonLeyton Orient 1-3 AFC Wimbledon | Sky Bet League One |
| 20 | Sat 24 Jan | 111-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 21 | Tue 27 Jan | 110-3 v Doncaster RoversDoncaster Rovers 3-0 Leyton Orient | Sky Bet League One |
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