| 1 | Sat 25 Aug 2018 | 1-1 v GatesheadGateshead 1-1 Leyton Orient | National League |
| 2 | Sat 1 Sep 2018 | 1-0 v ChesterfieldChesterfield 0-1 Leyton Orient | National League |
| 3 | Tue 4 Sep 2018 | 3-0 v Solihull MoorsLeyton Orient 3-0 Solihull Moors | National League |
| 4 | Sat 8 Sep 2018 | 1-1 v FC Halifax TownFC Halifax Town 1-1 Leyton Orient | National League |
| 5 | Sat 15 Sep 2018 | 3-1 v BarnetLeyton Orient 3-1 Barnet | National League |
| 6 | Sat 22 Sep 2018 | 3-0 v Harrogate TownHarrogate Town 0-3 Leyton Orient | National League |
| 7 | Sat 6 Oct 2018 | 2-0 v Maidenhead UnitedMaidenhead United 0-2 Leyton Orient | National League |
| 8 | Sat 13 Oct 2018 | 0-0 v Hartlepool UnitedLeyton Orient 0-0 Hartlepool United | National League |
| 9 | Tue 30 Oct 2018 | 1-1 v EastleighEastleigh 1-1 Leyton Orient | National League |
| 10 | Sat 24 Nov 2018 | 2-0 v WrexhamWrexham 0-2 Leyton Orient | National League |
| 11 | Sat 22 Dec 2018 | 3-1 v ChesterfieldLeyton Orient 3-1 Chesterfield | National League |
| 12 | Wed 26 Dec 2018 | 1-2 v Dagenham & RedbridgeDagenham & Redbridge 2-1 Leyton Orient | National League |
| 13 | Sat 29 Dec 2018 | 0-0 v Dover AthleticDover Athletic 0-0 Leyton Orient | National League |
| 14 | Tue 1 Jan 2019 | 1-0 v Dagenham & RedbridgeLeyton Orient 1-0 Dagenham & Redbridge | National League |
| 15 | Sat 26 Jan 2019 | 3-0 v Maidstone UnitedLeyton Orient 3-0 Maidstone United | National League |
| 16 | Sat 2 Feb 2019 | 1-0 v Blyth SpartansLeyton Orient 1-0 Blyth Spartans | Buildbase FA Trophy Third Round |
| 17 | Sat 9 Feb 2019 | 1-1 v Hartlepool UnitedHartlepool United 1-1 Leyton Orient | National League |
| 18 | Sat 2 Mar 2019 | 172-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Leyton Orient | National League |
| 19 | Sat 9 Mar 2019 | 171-0 v WrexhamLeyton Orient 1-0 Wrexham | National League |
| 20 | Tue 12 Mar 2019 | 172-1 v Aldershot TownAldershot Town 1-2 Leyton Orient | National League |
| 21 | Sat 16 Mar 2019 | 171-0 v AFC Telford UnitedLeyton Orient 1-0 AFC Telford United | Buildbase FA Trophy Semi Final |
| 22 | Sat 6 Apr 2019 | 172-2 v FC Halifax TownLeyton Orient 2-2 FC Halifax Town | National League |
| 23 | Tue 9 Apr 2019 | 173-2 v EastleighLeyton Orient 3-2 Eastleigh | National League |
| 24 | Sat 13 Apr 2019 | 172-1 v Sutton UnitedSutton United 1-2 Leyton Orient | National League |
| 25 | Fri 19 Apr 2019 | 172-0 v Harrogate TownLeyton Orient 2-0 Harrogate Town | National League |
| 26 | Mon 22 Apr 2019 | 170-0 v Solihull MoorsSolihull Moors 0-0 Leyton Orient | National League |
| 27 | Sat 27 Apr 2019 | 170-0 v Braintree TownLeyton Orient 0-0 Braintree Town | National League |
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