| 1 | Sat 6 Aug 2016 | 11-1 v Cheltenham TownCheltenham Town 1-1 Leyton Orient | Sky Bet League Two |
| 2 | Sat 13 Aug 2016 | 10-1 v Newport CountyLeyton Orient 0-1 Newport County | Sky Bet League Two |
| 3 | Tue 16 Aug 2016 | 13-0 v StevenageLeyton Orient 3-0 Stevenage | Sky Bet League Two |
| 4 | Sat 20 Aug 2016 | 12-1 v Grimsby TownGrimsby Town 1-2 Leyton Orient | Sky Bet League Two |
| 5 | Sat 27 Aug 2016 | 11-2 v Mansfield TownLeyton Orient 1-2 Mansfield Town | Sky Bet League Two |
| 6 | Sat 3 Sep 2016 | 12-1 v MorecambeMorecambe 1-2 Leyton Orient | Sky Bet League Two |
| 7 | Sat 10 Sep 2016 | 12-2 v Carlisle UnitedCarlisle United 2-2 Leyton Orient | Sky Bet League Two |
| 8 | Sat 17 Sep 2016 | 10-1 v Yeovil TownLeyton Orient 0-1 Yeovil Town | Sky Bet League Two |
| 9 | Sat 24 Sep 2016 | 11-3 v Notts CountyNotts County 3-1 Leyton Orient | Sky Bet League Two |
| 10 | Tue 27 Sep 2016 | 10-2 v Plymouth ArgyleLeyton Orient 0-2 Plymouth Argyle | Sky Bet League Two |
| 11 | Sat 1 Oct 2016 | 10-0 v BarnetBarnet 0-0 Leyton Orient | Sky Bet League Two |
| 12 | Sat 8 Oct 2016 | 10-1 v PortsmouthLeyton Orient 0-1 Portsmouth | Sky Bet League Two |
| 13 | Sat 15 Oct 2016 | 11-2 v Luton TownLeyton Orient 1-2 Luton Town | Sky Bet League Two |
| 14 | Sat 22 Oct 2016 | 13-1 v Hartlepool UnitedHartlepool United 1-3 Leyton Orient | Sky Bet League Two |
| 15 | Sat 29 Oct 2016 | 10-2 v Crewe AlexandraLeyton Orient 0-2 Crewe Alexandra | Sky Bet League Two |
| 16 | Sun 6 Nov 2016 | 10-6 v Sheffield UnitedSheffield United 6-0 Leyton Orient | Emirates FA Cup First Round |
| 17 | Sat 12 Nov 2016 | 13-0 v Colchester UnitedColchester United 0-3 Leyton Orient | Sky Bet League Two |
| 18 | Sat 19 Nov 2016 | 11-2 v BlackpoolLeyton Orient 1-2 Blackpool | Sky Bet League Two |
| 19 | Tue 22 Nov 2016 | 10-1 v Exeter CityLeyton Orient 0-1 Exeter City | Sky Bet League Two |
| 20 | Sat 26 Nov 2016 | 11-3 v Doncaster RoversDoncaster Rovers 3-1 Leyton Orient | Sky Bet League Two |
| 21 | Sat 10 Dec 2016 | 11-0 v Accrington StanleyLeyton Orient 1-0 Accrington Stanley | Sky Bet League Two |
| 22 | Sat 17 Dec 2016 | 10-1 v Wycombe WanderersWycombe Wanderers 1-0 Leyton Orient | Sky Bet League Two |
| 23 | Mon 26 Dec 2016 | 13-2 v Crawley TownLeyton Orient 3-2 Crawley Town | Sky Bet League Two |
| 24 | Sat 31 Dec 2016 | 11-1 v Cambridge UnitedLeyton Orient 1-1 Cambridge United | Sky Bet League Two |
| 25 | Mon 2 Jan 2017 | 10-4 v Exeter CityExeter City 4-0 Leyton Orient | Sky Bet League Two |
| 26 | Sat 7 Jan 2017 | 11-3 v BarnetLeyton Orient 1-3 Barnet | Sky Bet League Two |
| 27 | Sat 14 Jan 2017 | 11-2 v PortsmouthPortsmouth 2-1 Leyton Orient | Sky Bet League Two |
| 28 | Sat 28 Jan 2017 | 10-2 v Mansfield TownMansfield Town 2-0 Leyton Orient | Sky Bet League Two |
| 29 | Sat 18 Mar 2017 | 11-4 v Doncaster RoversLeyton Orient 1-4 Doncaster Rovers | Sky Bet League Two |
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