| 1 | Tue 10 Dec | 23 0-2 v Leyton OrientCharlton Athletic 0-2 Leyton Orient | EFL Trophy Second Round |
| 2 | Tue 11 Feb | 453-0 v Mansfield TownLeyton Orient 3-0 Mansfield Town | Sky Bet League One |
| 3 | Sat 15 Feb | 453-2 v Lincoln CityLeyton Orient 3-2 Lincoln City | Sky Bet League One |
| 4 | Tue 18 Feb | 452-1 v WrexhamWrexham 1-2 Leyton Orient | Sky Bet League One |
| 5 | Sat 22 Feb | 451-2 v Bolton WanderersBolton Wanderers 2-1 Leyton Orient | Sky Bet League One |
| 6 | Tue 25 Feb | 450-2 v Birmingham CityBirmingham City 2-0 Leyton Orient | Sky Bet League One |
| 7 | Sat 1 Mar | 451-2 v Charlton AthleticLeyton Orient 1-2 Charlton Athletic | Sky Bet League One |
| 8 | Tue 4 Mar | 450-1 v Rotherham UnitedRotherham United 1-0 Leyton Orient | Sky Bet League One |
| 9 | Sat 8 Mar | 451-2 v Northampton TownLeyton Orient 1-2 Northampton Town | Sky Bet League One |
| 10 | Sat 15 Mar | 452-1 v BlackpoolBlackpool 1-2 Leyton Orient | Sky Bet League One |
| 11 | Thu 27 Mar | 451-0 v StevenageLeyton Orient 1-0 Stevenage | Sky Bet League One |
| 12 | Tue 1 Apr | 451-2 v Burton AlbionBurton Albion 2-1 Leyton Orient | Sky Bet League One |
| 13 | Tue 8 Apr | 453-2 v Mansfield TownMansfield Town 2-3 Leyton Orient | Sky Bet League One |
| 14 | Sat 12 Apr | 453-1 v Crawley TownCrawley Town 1-3 Leyton Orient | Sky Bet League One |
| 15 | Fri 18 Apr | 454-3 v BarnsleyLeyton Orient 4-3 Barnsley | Sky Bet League One |
| 16 | Mon 21 Apr | 452-1 v Cambridge UnitedCambridge United 1-2 Leyton Orient | Sky Bet League One |
| 17 | Sat 26 Apr | 451-0 v Wycombe WanderersLeyton Orient 1-0 Wycombe Wanderers | Sky Bet League One |
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