| 1 | Sat 25 Aug 2018 | 1-1 v GatesheadGateshead 1-1 Leyton Orient | National League |
| 2 | Sat 15 Sep 2018 | 3-1 v BarnetLeyton Orient 3-1 Barnet | National League |
| 3 | Sat 22 Sep 2018 | 3-0 v Harrogate TownHarrogate Town 0-3 Leyton Orient | National League |
| 4 | Sat 29 Sep 2018 | 0-1 v Sutton UnitedLeyton Orient 0-1 Sutton United | National League |
| 5 | Sat 6 Oct 2018 | 2-0 v Maidenhead UnitedMaidenhead United 0-2 Leyton Orient | National League |
| 6 | Sat 3 Nov 2018 | 3-1 v AFC FyldeAFC Fylde 1-3 Leyton Orient | National League |
| 7 | Sat 17 Nov 2018 | 3-1 v BromleyLeyton Orient 3-1 Bromley | National League |
| 8 | Sat 24 Nov 2018 | 2-0 v WrexhamWrexham 0-2 Leyton Orient | National League |
| 9 | Tue 27 Nov 2018 | 0-0 v Aldershot TownLeyton Orient 0-0 Aldershot Town | National League |
| 10 | Sat 1 Dec 2018 | 2-0 v GatesheadLeyton Orient 2-0 Gateshead | National League |
| 11 | Sat 8 Dec 2018 | 0-1 v Boreham WoodBoreham Wood 1-0 Leyton Orient | National League |
| 12 | Sat 22 Dec 2018 | 3-1 v ChesterfieldLeyton Orient 3-1 Chesterfield | National League |
| 13 | Wed 26 Dec 2018 | 1-2 v Dagenham & RedbridgeDagenham & Redbridge 2-1 Leyton Orient | National League |
| 14 | Sat 29 Dec 2018 | 0-0 v Dover AthleticDover Athletic 0-0 Leyton Orient | National League |
| 15 | Tue 1 Jan 2019 | 1-0 v Dagenham & RedbridgeLeyton Orient 1-0 Dagenham & Redbridge | National League |
| 16 | Sat 5 Jan 2019 | 0-3 v Salford CityLeyton Orient 0-3 Salford City | National League |
| 17 | Sat 2 Feb 2019 | 1-0 v Blyth SpartansLeyton Orient 1-0 Blyth Spartans | Buildbase FA Trophy Third Round |
| 18 | Sat 16 Mar 2019 | 1-0 v AFC Telford UnitedLeyton Orient 1-0 AFC Telford United | Buildbase FA Trophy Semi Final |
| 19 | Tue 26 Mar 2019 | 2-0 v AFC FyldeLeyton Orient 2-0 AFC Fylde | National League |
| 20 | Sat 13 Apr 2019 | 2-1 v Sutton UnitedSutton United 1-2 Leyton Orient | National League |
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