| 1 | Sun 10 Nov 2019 | 1-0 v Southend UnitedDover Athletic 1-0 Southend United | Emirates FA Cup First Round |
| 2 | Tue 26 Nov 2019 | 3-4 v Maidenhead UnitedDover Athletic 3-4 Maidenhead United | Vanarama National League |
| 3 | Thu 26 Dec 2019 | 1-3 v Colchester UnitedLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 4 | Sun 29 Dec 2019 | 1-1 v Newport CountyNewport County 1-1 Leyton Orient | Sky Bet League Two |
| 5 | Wed 1 Jan 2020 | 0-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
| 6 | Tue 21 Jan 2020 | 1-1 v Northampton TownLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 7 | Sat 25 Jan 2020 | 2-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 8 | Tue 28 Jan 2020 | 0-2 v Crewe AlexandraCrewe Alexandra 2-0 Leyton Orient | Sky Bet League Two |
| 9 | Sat 1 Feb 2020 | 3-0 v StevenageStevenage 0-3 Leyton Orient | Sky Bet League Two |
| 10 | Sat 8 Feb 2020 | 1-1 v Macclesfield TownLeyton Orient 1-1 Macclesfield Town | Sky Bet League Two |
| 11 | Sat 22 Feb 2020 | 2-2 v Oldham AthleticLeyton Orient 2-2 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 7 Mar 2020 | 2-1 v Cambridge UnitedLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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