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