| 1 | Sat 4 Aug 2018 | 1-1 v Salford CitySalford City 1-1 Leyton Orient | National League |
| 2 | Tue 7 Aug 2018 | 1-1 v Ebbsfleet UnitedLeyton Orient 1-1 Ebbsfleet United | National League |
| 3 | Sat 11 Aug 2018 | 2-2 v BarrowLeyton Orient 2-2 Barrow | National League |
| 4 | Tue 14 Aug 2018 | 2-1 v Maidstone UnitedMaidstone United 1-2 Leyton Orient | National League |
| 5 | Sat 18 Aug 2018 | 1-0 v Boreham WoodLeyton Orient 1-0 Boreham Wood | National League |
| 6 | Sat 25 Aug 2018 | 1-1 v GatesheadGateshead 1-1 Leyton Orient | National League |
| 7 | Sat 8 Sep 2018 | 1-1 v FC Halifax TownFC Halifax Town 1-1 Leyton Orient | National League |
| 8 | Sat 15 Sep 2018 | 3-1 v BarnetLeyton Orient 3-1 Barnet | National League |
| 9 | Sat 22 Sep 2018 | 3-0 v Harrogate TownHarrogate Town 0-3 Leyton Orient | National League |
| 10 | Sat 29 Sep 2018 | 0-1 v Sutton UnitedLeyton Orient 0-1 Sutton United | National League |
| 11 | Sat 6 Oct 2018 | 2-0 v Maidenhead UnitedMaidenhead United 0-2 Leyton Orient | National League |
| 12 | Sat 13 Oct 2018 | 0-0 v Hartlepool UnitedLeyton Orient 0-0 Hartlepool United | National League |
| 13 | Sat 3 Nov 2018 | 3-1 v AFC FyldeAFC Fylde 1-3 Leyton Orient | National League |
| 14 | Sat 17 Nov 2018 | 3-1 v BromleyLeyton Orient 3-1 Bromley | National League |
| 15 | Sat 24 Nov 2018 | 2-0 v WrexhamWrexham 0-2 Leyton Orient | National League |
| 16 | Tue 27 Nov 2018 | 0-0 v Aldershot TownLeyton Orient 0-0 Aldershot Town | National League |
| 17 | Sat 1 Dec 2018 | 2-0 v GatesheadLeyton Orient 2-0 Gateshead | National League |
| 18 | Sat 8 Dec 2018 | 0-1 v Boreham WoodBoreham Wood 1-0 Leyton Orient | National League |
| 19 | Sat 22 Dec 2018 | 3-1 v ChesterfieldLeyton Orient 3-1 Chesterfield | National League |
| 20 | Wed 26 Dec 2018 | 1-2 v Dagenham & RedbridgeDagenham & Redbridge 2-1 Leyton Orient | National League |
| 21 | Sat 29 Dec 2018 | 0-0 v Dover AthleticDover Athletic 0-0 Leyton Orient | National League |
| 22 | Sat 19 Jan 2019 | 0-2 v Ebbsfleet UnitedEbbsfleet United 2-0 Leyton Orient | National League |
| 23 | Sat 2 Feb 2019 | 1-0 v Blyth SpartansLeyton Orient 1-0 Blyth Spartans | Buildbase FA Trophy Third Round |
| 24 | Sat 9 Feb 2019 | 1-1 v Hartlepool UnitedHartlepool United 1-1 Leyton Orient | National League |
| 25 | Tue 26 Mar 2019 | 272-0 v AFC FyldeLeyton Orient 2-0 AFC Fylde | National League |
| 26 | Tue 2 Apr 2019 | 271-2 v BromleyBromley 2-1 Leyton Orient | National League |
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