| 1 | Sat 9 Aug 2014 | 11-2 v ChesterfieldLeyton Orient 1-2 Chesterfield | Sky Bet League One |
| 2 | Sat 16 Aug 2014 | 13-1 v Oldham AthleticOldham Athletic 1-3 Leyton Orient | Sky Bet League One |
| 3 | Tue 19 Aug 2014 | 10-0 v Bristol CityBristol City 0-0 Leyton Orient | Sky Bet League One |
| 4 | Sat 23 Aug 2014 | 10-0 v WalsallLeyton Orient 0-0 Walsall | Sky Bet League One |
| 5 | Sat 30 Aug 2014 | 11-1 v Fleetwood TownFleetwood Town 1-1 Leyton Orient | Sky Bet League One |
| 6 | Tue 11 Nov 2014 | 12-0 v Northampton TownLeyton Orient 2-0 Northampton Town | Johnstone's Paint Trophy Southern Area Quarter Final |
| 7 | Sat 15 Nov 2014 | 12-3 v GillinghamGillingham 3-2 Leyton Orient | Sky Bet League One |
| 8 | Sat 22 Nov 2014 | 14-1 v Crewe AlexandraLeyton Orient 4-1 Crewe Alexandra | Sky Bet League One |
| 9 | Sat 29 Nov 2014 | 11-3 v Bradford CityBradford City 3-1 Leyton Orient | Sky Bet League One |
| 10 | Sat 6 Dec 2014 | 10-1 v GillinghamGillingham 1-0 Leyton Orient | Johnstone's Paint Trophy Southern Area Semi Final |
| 11 | Sat 13 Dec 2014 | 11-2 v Peterborough UnitedLeyton Orient 1-2 Peterborough United | Sky Bet League One |
| 12 | Sat 20 Dec 2014 | 10-2 v BarnsleyBarnsley 2-0 Leyton Orient | Sky Bet League One |
| 13 | Fri 26 Dec 2014 | 14-1 v Crawley TownLeyton Orient 4-1 Crawley Town | Sky Bet League One |
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