| 1 | Sat 3 Aug 2013 | 15-1 v Carlisle UnitedCarlisle United 1-5 Leyton Orient | Sky Bet League One |
| 2 | Tue 6 Aug 2013 | 13-2 v Coventry CityLeyton Orient 3-2 Coventry City | Capital One Cup First Round |
| 3 | Sat 10 Aug 2013 | 13-0 v Shrewsbury TownLeyton Orient 3-0 Shrewsbury Town | Sky Bet League One |
| 4 | Sat 17 Aug 2013 | 11-0 v StevenageStevenage 0-1 Leyton Orient | Sky Bet League One |
| 5 | Sat 24 Aug 2013 | 12-0 v Crewe AlexandraLeyton Orient 2-0 Crewe Alexandra | Sky Bet League One |
| 6 | Tue 27 Aug 2013 | 10-1 v Hull CityLeyton Orient 0-1 Hull City | Capital One Cup Second Round |
| 7 | Sat 31 Aug 2013 | 12-1 v Colchester UnitedColchester United 1-2 Leyton Orient | Sky Bet League One |
| 8 | Tue 3 Sep 2013 | 13-1 v GillinghamGillingham 1-3 Leyton Orient | Johnstone's Paint Trophy Southern Area First Round |
| 9 | Sat 14 Sep 2013 | 13-2 v Port ValeLeyton Orient 3-2 Port Vale | Sky Bet League One |
| 10 | Tue 17 Sep 2013 | 15-1 v Notts CountyLeyton Orient 5-1 Notts County | Sky Bet League One |
| 11 | Mon 23 Sep 2013 | 12-0 v BrentfordBrentford 0-2 Leyton Orient | Sky Bet League One |
| 12 | Sat 28 Sep 2013 | 11-1 v WalsallLeyton Orient 1-1 Walsall | Sky Bet League One |
| 13 | Sat 5 Oct 2013 | 11-1 v Oldham AthleticOldham Athletic 1-1 Leyton Orient | Sky Bet League One |
| 14 | Tue 8 Oct 2013 | 10-0 v Coventry CityLeyton Orient 0-0 Coventry City | Johnstone's Paint Trophy Southern Area Second Round |
| 15 | Sat 12 Oct 2013 | 12-1 v Milton Keynes DonsLeyton Orient 2-1 Milton Keynes Dons | Sky Bet League One |
| 16 | Sat 19 Oct 2013 | 14-0 v Tranmere RoversTranmere Rovers 0-4 Leyton Orient | Sky Bet League One |
| 17 | Tue 22 Oct 2013 | 11-3 v Coventry CityCoventry City 3-1 Leyton Orient | Sky Bet League One |
| 18 | Sat 26 Oct 2013 | 11-0 v Rotherham UnitedLeyton Orient 1-0 Rotherham United | Sky Bet League One |
| 19 | Sat 2 Nov 2013 | 13-1 v Peterborough UnitedPeterborough United 1-3 Leyton Orient | Sky Bet League One |
| 20 | Tue 12 Nov 2013 | 12-3 v StevenageStevenage 3-2 Leyton Orient | Johnstone's Paint Trophy Southern Area Quarter Final |
| 21 | Sat 16 Nov 2013 | 10-1 v Preston North EndLeyton Orient 0-1 Preston North End | Sky Bet League One |
| 22 | Sat 23 Nov 2013 | 13-1 v Swindon TownSwindon Town 1-3 Leyton Orient | Sky Bet League One |
| 23 | Tue 26 Nov 2013 | 12-2 v Bristol CityBristol City 2-2 Leyton Orient | Sky Bet League One |
| 24 | Sat 30 Nov 2013 | 11-1 v Sheffield UnitedLeyton Orient 1-1 Sheffield United | Sky Bet League One |
| 25 | Sat 7 Dec 2013 | 11-0 v WalsallLeyton Orient 1-0 Walsall | FA Cup with Budweiser Second Round |
| 26 | Sat 14 Dec 2013 | 11-1 v Bradford CityBradford City 1-1 Leyton Orient | Sky Bet League One |
| 27 | Sat 21 Dec 2013 | 12-3 v Crawley TownLeyton Orient 2-3 Crawley Town | Sky Bet League One |
| 28 | Sat 29 Mar 2014 | 10-1 v Bradford CityLeyton Orient 0-1 Bradford City | Sky Bet League One |
| 29 | Sat 5 Apr 2014 | 11-1 v Sheffield UnitedSheffield United 1-1 Leyton Orient | Sky Bet League One |
| 30 | Sat 12 Apr 2014 | 15-1 v GillinghamLeyton Orient 5-1 Gillingham | Sky Bet League One |
| 31 | Fri 18 Apr 2014 | 11-2 v Crawley TownCrawley Town 2-1 Leyton Orient | Sky Bet League One |
| 32 | Mon 21 Apr 2014 | 11-3 v Wolverhampton WanderersLeyton Orient 1-3 Wolverhampton Wanderers | Sky Bet League One |
| 33 | Sat 26 Apr 2014 | 12-0 v Tranmere RoversLeyton Orient 2-0 Tranmere Rovers | Sky Bet League One |
| 34 | Sat 3 May 2014 | 13-1 v Milton Keynes DonsMilton Keynes Dons 1-3 Leyton Orient | Sky Bet League One |
| 35 | Sat 10 May 2014 | 11-1 v Peterborough UnitedPeterborough United 1-1 Leyton Orient | Sky Bet League One Play-off Semi Final |
| 36 | Tue 13 May 2014 | 12-1 v Peterborough UnitedLeyton Orient 2-1 Peterborough United | Sky Bet League One Play-off Semi Final |
| 37 | Sun 25 May 2014 | 12-2 v Rotherham UnitedLeyton Orient 2-2 Rotherham United | Sky Bet League One Play-off Final |
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