| 1 | Tue 3 Sep 2019 | 2-0 v Southend UnitedLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 2 | Sat 14 Sep 2019 | 2-2 v Exeter CityExeter City 2-2 Leyton Orient | Sky Bet League Two |
| 3 | Tue 17 Sep 2019 | 1-2 v Crewe AlexandraLeyton Orient 1-2 Crewe Alexandra | Sky Bet League Two |
| 4 | Sat 21 Sep 2019 | 1-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 5 | Sat 28 Sep 2019 | 3-3 v Port ValeLeyton Orient 3-3 Port Vale | Sky Bet League Two |
| 6 | Sat 5 Oct 2019 | 1-0 v Northampton TownNorthampton Town 0-1 Leyton Orient | Sky Bet League Two |
| 7 | Tue 8 Oct 2019 | 0-3 v AFC WimbledonAFC Wimbledon 3-0 Leyton Orient | Leasing.com Trophy Southern Group C |
| 8 | Sat 12 Oct 2019 | 3-1 v WalsallLeyton Orient 3-1 Walsall | Sky Bet League Two |
| 9 | Sat 19 Oct 2019 | 4-0 v Grimsby TownGrimsby Town 0-4 Leyton Orient | Sky Bet League Two |
| 10 | Sat 26 Oct 2019 | 1-1 v Carlisle UnitedLeyton Orient 1-1 Carlisle United | Sky Bet League Two |
| 11 | Sat 2 Nov 2019 | 0-1 v MorecambeMorecambe 1-0 Leyton Orient | Sky Bet League Two |
| 12 | Sat 14 Dec 2019 | 0-0 v Bradford CityLeyton Orient 0-0 Bradford City | Sky Bet League Two |
| 13 | Sat 21 Dec 2019 | 3-2 v Cambridge UnitedCambridge United 2-3 Leyton Orient | Sky Bet League Two |
| 14 | Thu 26 Dec 2019 | 1-3 v Colchester UnitedLeyton Orient 1-3 Colchester United | Sky Bet League Two |
| 15 | Sun 29 Dec 2019 | 1-1 v Newport CountyNewport County 1-1 Leyton Orient | Sky Bet League Two |
| 16 | Wed 1 Jan 2020 | 0-1 v WalsallWalsall 1-0 Leyton Orient | Sky Bet League Two |
| 17 | Sat 11 Jan 2020 | 1-1 v Grimsby TownLeyton Orient 1-1 Grimsby Town | Sky Bet League Two |
| 18 | Sat 18 Jan 2020 | 0-1 v Port ValePort Vale 1-0 Leyton Orient | Sky Bet League Two |
| 19 | Tue 21 Jan 2020 | 1-1 v Northampton TownLeyton Orient 1-1 Northampton Town | Sky Bet League Two |
| 20 | Sat 25 Jan 2020 | 2-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 21 | Tue 28 Jan 2020 | 0-2 v Crewe AlexandraCrewe Alexandra 2-0 Leyton Orient | Sky Bet League Two |
| 22 | Sat 1 Feb 2020 | 3-0 v StevenageStevenage 0-3 Leyton Orient | Sky Bet League Two |
| 23 | Sat 8 Feb 2020 | 1-1 v Macclesfield TownLeyton Orient 1-1 Macclesfield Town | Sky Bet League Two |
| 24 | Tue 11 Feb 2020 | 2-1 v Mansfield TownLeyton Orient 2-1 Mansfield Town | Sky Bet League Two |
| 25 | Sat 15 Feb 2020 | 1-2 v Cheltenham TownCheltenham Town 2-1 Leyton Orient | Sky Bet League Two |
| 26 | Sat 22 Feb 2020 | 2-2 v Oldham AthleticLeyton Orient 2-2 Oldham Athletic | Sky Bet League Two |
| 27 | Sat 7 Mar 2020 | 2-1 v Cambridge UnitedLeyton Orient 2-1 Cambridge United | Sky Bet League Two |
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