| 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 13 Oct 2018 | 0-0 v Hartlepool UnitedLeyton Orient 0-0 Hartlepool United | National League |
| 6 | Sat 27 Oct 2018 | 4-0 v Havant & WaterloovilleLeyton Orient 4-0 Havant & Waterlooville | National League |
| 7 | Sat 1 Dec 2018 | 2-0 v GatesheadLeyton Orient 2-0 Gateshead | National League |
| 8 | Sat 8 Dec 2018 | 0-1 v Boreham WoodBoreham Wood 1-0 Leyton Orient | National League |
| 9 | Sat 22 Dec 2018 | 3-1 v ChesterfieldLeyton Orient 3-1 Chesterfield | National League |
| 10 | Wed 26 Dec 2018 | 1-2 v Dagenham & RedbridgeDagenham & Redbridge 2-1 Leyton Orient | National League |
| 11 | Sat 29 Dec 2018 | 0-0 v Dover AthleticDover Athletic 0-0 Leyton Orient | National League |
| 12 | Tue 1 Jan 2019 | 1-0 v Dagenham & RedbridgeLeyton Orient 1-0 Dagenham & Redbridge | National League |
| 13 | Sat 5 Jan 2019 | 0-3 v Salford CityLeyton Orient 0-3 Salford City | National League |
| 14 | Sat 19 Jan 2019 | 0-2 v Ebbsfleet UnitedEbbsfleet United 2-0 Leyton Orient | National League |
| 15 | Sat 26 Jan 2019 | 3-0 v Maidstone UnitedLeyton Orient 3-0 Maidstone United | National League |
| 16 | Sat 16 Feb 2019 | 0-1 v Maidenhead UnitedLeyton Orient 0-1 Maidenhead United | National League |
| 17 | Sat 2 Mar 2019 | 2-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Leyton Orient | National League |
| 18 | Tue 5 Mar 2019 | 3-2 v BarrowBarrow 2-3 Leyton Orient | National League |
| 19 | Sat 9 Mar 2019 | 1-0 v WrexhamLeyton Orient 1-0 Wrexham | National League |
| 20 | Tue 12 Mar 2019 | 2-1 v Aldershot TownAldershot Town 1-2 Leyton Orient | National League |
| 21 | Sat 16 Mar 2019 | 1-0 v AFC Telford UnitedLeyton Orient 1-0 AFC Telford United | Buildbase FA Trophy Semi Final |
| 22 | Tue 9 Apr 2019 | 3-2 v EastleighLeyton Orient 3-2 Eastleigh | National League |
| 23 | Sat 13 Apr 2019 | 2-1 v Sutton UnitedSutton United 1-2 Leyton Orient | National League |
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