| 1 | Tue 15 Aug | 4 2-3 v Wycombe WanderersWycombe Wanderers 3-2 Leyton Orient | Sky Bet League One |
| 2 | Sat 19 Aug | 4 0-0 v BlackpoolBlackpool 0-0 Leyton Orient | Sky Bet League One |
| 3 | Sat 26 Aug | 42-0 v Cambridge UnitedLeyton Orient 2-0 Cambridge United | Sky Bet League One |
| 4 | Sat 2 Sep | 4 0-3 v StevenageLeyton Orient 0-3 Stevenage | Sky Bet League One |
| 5 | Sat 7 Oct | 42-1 v ReadingLeyton Orient 2-1 Reading | Sky Bet League One |
| 6 | Sat 14 Oct | 4 1-0 v Carlisle UnitedCarlisle United 0-1 Leyton Orient | Sky Bet League One |
| 7 | Tue 24 Oct | 4 2-2 v Northampton TownNorthampton Town 2-2 Leyton Orient | Sky Bet League One |
| 8 | Sat 4 Nov | 43-1 v Carlisle UnitedLeyton Orient 3-1 Carlisle United | Emirates FA Cup First Round |
| 9 | Tue 7 Nov | 41-2 v PortsmouthLeyton Orient 1-2 Portsmouth | EFL Trophy |
| 10 | Sat 11 Nov | 42-3 v Oxford UnitedLeyton Orient 2-3 Oxford United | Sky Bet League One |
| 11 | Tue 21 Nov | 40-1 v Lincoln CityLeyton Orient 0-1 Lincoln City | Sky Bet League One |
| 12 | Sat 25 Nov | 41-1 v Wigan AthleticLeyton Orient 1-1 Wigan Athletic | Sky Bet League One |
| 13 | Tue 28 Nov | 4 1-1 v Bristol RoversBristol Rovers 1-1 Leyton Orient | Sky Bet League One |
| 14 | Sun 3 Dec | 40-1 v ChesterfieldChesterfield 1-0 Leyton Orient | Emirates FA Cup Second Round |
| 15 | Sat 13 Jan | 43-0 v PortsmouthPortsmouth 0-3 Leyton Orient | Sky Bet League One |
| 16 | Sat 3 Feb | 120-0 v Tranmere RoversTranmere Rovers 0-0 Crewe Alexandra | Sky Bet League Two |
| 17 | Sat 10 Feb | 121-0 v Crawley TownCrewe Alexandra 1-0 Crawley Town | Sky Bet League Two |
| 18 | Tue 13 Feb | 123-1 v Stockport CountyStockport County 1-3 Crewe Alexandra | Sky Bet League Two |
| 19 | Sat 17 Feb | 120-0 v Harrogate TownCrewe Alexandra 0-0 Harrogate Town | Sky Bet League Two |
| 20 | Sat 24 Feb | 12 3-1 v Notts CountyNotts County 1-3 Crewe Alexandra | Sky Bet League Two |
| 21 | Sat 2 Mar | 122-3 v MorecambeCrewe Alexandra 2-3 Morecambe | Sky Bet League Two |
| 22 | Sat 9 Mar | 120-2 v Doncaster RoversDoncaster Rovers 2-0 Crewe Alexandra | Sky Bet League Two |
| 23 | Tue 12 Mar | 121-0 v Sutton UnitedCrewe Alexandra 1-0 Sutton United | Sky Bet League Two |
| 24 | Sat 16 Mar | 12 1-3 v Milton Keynes DonsMilton Keynes Dons 3-1 Crewe Alexandra | Sky Bet League Two |
| 25 | Sat 23 Mar | 121-1 v AFC WimbledonCrewe Alexandra 1-1 AFC Wimbledon | Sky Bet League Two |
| 26 | Fri 29 Mar | 12 0-0 v GillinghamGillingham 0-0 Crewe Alexandra | Sky Bet League Two |
| 27 | Mon 1 Apr | 120-3 v Forest Green RoversCrewe Alexandra 0-3 Forest Green Rovers | Sky Bet League Two |
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