| 1 | 5/9/2020 | 42-1 v Forest Green RoversForest Green Rovers 1-2 Leyton Orient | Carabao Cup First Round South |
| 2 | 15/9/2020 | 43-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 3 | 19/9/2020 | 42-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 4 | 3/10/2020 | 4 0-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 5 | 10/10/2020 | 4 1-1 v BarrowBarrow 1-1 Leyton Orient | Sky Bet League Two |
| 6 | 13/10/2020 | 41-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 7 | 17/10/2020 | 42-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 8 | 20/10/2020 | 41-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 9 | 24/10/2020 | 42-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 10 | 27/10/2020 | 4 1-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 11 | 31/10/2020 | 4 4-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 12 | 3/11/2020 | 41-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 13 | 10/11/2020 | 41-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Checkatrade Trophy Group 10 |
| 14 | 14/11/2020 | 41-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 15 | 21/11/2020 | 43-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 16 | 24/11/2020 | 41-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 17 | 28/11/2020 | 43-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 18 | 5/12/2020 | 40-2 v Scunthorpe UnitedScunthorpe United 2-0 Leyton Orient | Sky Bet League Two |
| 19 | 12/12/2020 | 42-1 v Newport CountyLeyton Orient 2-1 Newport County | Sky Bet League Two |
| 20 | 15/12/2020 | 41-2 v MorecambeMorecambe 2-1 Leyton Orient | Sky Bet League Two |
| 21 | 19/12/2020 | 41-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 22 | 26/12/2020 | 41-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 23 | 29/12/2020 | 42-0 v Southend UnitedLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 24 | 2/1/2021 | 41-0 v Salford CityLeyton Orient 1-0 Salford City | Sky Bet League Two |
| 25 | 16/1/2021 | 42-0 v MorecambeLeyton Orient 2-0 Morecambe | Sky Bet League Two |
| 26 | 23/1/2021 | 40-1 v Forest Green RoversLeyton Orient 0-1 Forest Green Rovers | Sky Bet League Two |
| 27 | 30/1/2021 | 40-2 v Bolton WanderersBolton Wanderers 2-0 Leyton Orient | Sky Bet League Two |
| 28 | 2/2/2021 | 40-0 v Crawley TownCrawley Town 0-0 Leyton Orient | Sky Bet League Two |
| 29 | 6/2/2021 | 40-0 v Colchester UnitedLeyton Orient 0-0 Colchester United | Sky Bet League Two |
| 30 | 20/2/2021 | 41-1 v Port ValeLeyton Orient 1-1 Port Vale | Sky Bet League Two |
| 31 | 23/2/2021 | 4 0-1 v Bradford CityBradford City 1-0 Leyton Orient | Sky Bet League Two |
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