| 1 | 17/7/2018 | 4-0 v East Thurrock UnitedEast Thurrock United 0-4 Leyton Orient | Friendly |
| 2 | 4/8/2018 | 1-1 v Salford CitySalford City 1-1 Leyton Orient | National League |
| 3 | 7/8/2018 | 1-1 v Ebbsfleet UnitedLeyton Orient 1-1 Ebbsfleet United | National League |
| 4 | 11/8/2018 | 2-2 v BarrowLeyton Orient 2-2 Barrow | National League |
| 5 | 14/8/2018 | 2-1 v Maidstone UnitedMaidstone United 1-2 Leyton Orient | National League |
| 6 | 18/8/2018 | 1-0 v Boreham WoodLeyton Orient 1-0 Boreham Wood | National League |
| 7 | 25/8/2018 | 1-1 v GatesheadGateshead 1-1 Leyton Orient | National League |
| 8 | 27/8/2018 | 3-0 v Dover AthleticLeyton Orient 3-0 Dover Athletic | National League |
| 9 | 1/9/2018 | 1-0 v ChesterfieldChesterfield 0-1 Leyton Orient | National League |
| 10 | 4/9/2018 | 3-0 v Solihull MoorsLeyton Orient 3-0 Solihull Moors | National League |
| 11 | 8/9/2018 | 1-1 v FC Halifax TownFC Halifax Town 1-1 Leyton Orient | National League |
| 12 | 15/9/2018 | 3-1 v BarnetLeyton Orient 3-1 Barnet | National League |
| 13 | 22/9/2018 | 3-0 v Harrogate TownHarrogate Town 0-3 Leyton Orient | National League |
| 14 | 25/9/2018 | 5-1 v Braintree TownBraintree Town 1-5 Leyton Orient | National League |
| 15 | 29/9/2018 | 0-1 v Sutton UnitedLeyton Orient 0-1 Sutton United | National League |
| 16 | 6/10/2018 | 2-0 v Maidenhead UnitedMaidenhead United 0-2 Leyton Orient | National League |
| 17 | 13/10/2018 | 0-0 v Hartlepool UnitedLeyton Orient 0-0 Hartlepool United | National League |
| 18 | 27/10/2018 | 4-0 v Havant & WaterloovilleLeyton Orient 4-0 Havant & Waterlooville | National League |
| 19 | 30/10/2018 | 1-1 v EastleighEastleigh 1-1 Leyton Orient | National League |
| 20 | 3/11/2018 | 3-1 v AFC FyldeAFC Fylde 1-3 Leyton Orient | National League |
| 21 | 17/11/2018 | 3-1 v BromleyLeyton Orient 3-1 Bromley | National League |
| 22 | 24/11/2018 | 2-0 v WrexhamWrexham 0-2 Leyton Orient | National League |
| 23 | 27/11/2018 | 0-0 v Aldershot TownLeyton Orient 0-0 Aldershot Town | National League |
| 24 | 1/12/2018 | 2-0 v GatesheadLeyton Orient 2-0 Gateshead | National League |
| 25 | 8/12/2018 | 0-1 v Boreham WoodBoreham Wood 1-0 Leyton Orient | National League |
| 26 | 22/12/2018 | 3-1 v ChesterfieldLeyton Orient 3-1 Chesterfield | National League |
| 27 | 26/12/2018 | 1-2 v Dagenham & RedbridgeDagenham & Redbridge 2-1 Leyton Orient | National League |
| 28 | 29/12/2018 | 0-0 v Dover AthleticDover Athletic 0-0 Leyton Orient | National League |
| 29 | 1/1/2019 | 1-0 v Dagenham & RedbridgeLeyton Orient 1-0 Dagenham & Redbridge | National League |
| 30 | 5/1/2019 | 0-3 v Salford CityLeyton Orient 0-3 Salford City | National League |
| 31 | 19/1/2019 | 0-2 v Ebbsfleet UnitedEbbsfleet United 2-0 Leyton Orient | National League |
| 32 | 26/1/2019 | 3-0 v Maidstone UnitedLeyton Orient 3-0 Maidstone United | National League |
| 33 | 2/2/2019 | 1-0 v Blyth SpartansLeyton Orient 1-0 Blyth Spartans | Buildbase FA Trophy Third Round |
| 34 | 9/2/2019 | 1-1 v Hartlepool UnitedHartlepool United 1-1 Leyton Orient | National League |
| 35 | 16/2/2019 | 0-1 v Maidenhead UnitedLeyton Orient 0-1 Maidenhead United | National League |
| 36 | 2/3/2019 | 2-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Leyton Orient | National League |
| 37 | 5/3/2019 | 3-2 v BarrowBarrow 2-3 Leyton Orient | National League |
| 38 | 9/3/2019 | 1-0 v WrexhamLeyton Orient 1-0 Wrexham | National League |
| 39 | 12/3/2019 | 2-1 v Aldershot TownAldershot Town 1-2 Leyton Orient | National League |
| 40 | 16/3/2019 | 1-0 v AFC Telford UnitedLeyton Orient 1-0 AFC Telford United | Buildbase FA Trophy Semi Final |
| 41 | 26/3/2019 | 2-0 v AFC FyldeLeyton Orient 2-0 AFC Fylde | National League |
| 42 | 30/3/2019 | 0-0 v BarnetBarnet 0-0 Leyton Orient | National League |
| 43 | 2/4/2019 | 1-2 v BromleyBromley 2-1 Leyton Orient | National League |
| 44 | 6/4/2019 | 2-2 v FC Halifax TownLeyton Orient 2-2 FC Halifax Town | National League |
| 45 | 9/4/2019 | 3-2 v EastleighLeyton Orient 3-2 Eastleigh | National League |
| 46 | 13/4/2019 | 2-1 v Sutton UnitedSutton United 1-2 Leyton Orient | National League |
| 47 | 19/4/2019 | 2-0 v Harrogate TownLeyton Orient 2-0 Harrogate Town | National League |
| 48 | 22/4/2019 | 0-0 v Solihull MoorsSolihull Moors 0-0 Leyton Orient | National League |
| 49 | 27/4/2019 | 0-0 v Braintree TownLeyton Orient 0-0 Braintree Town | National League |
| 50 | 19/5/2019 | 0-1 v AFC FyldeAFC Fylde 1-0 Leyton Orient | Buildbase FA Trophy Final |
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