| 1 | 5/9/2020 | 102-1 v Forest Green RoversForest Green Rovers 1-2 Leyton Orient | Carabao Cup First Round South |
| 2 | 15/9/2020 | 103-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 3 | 19/9/2020 | 102-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 4 | 3/10/2020 | 100-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 5 | 6/10/2020 | 102-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Checkatrade Trophy Group 10 |
| 6 | 10/10/2020 | 101-1 v BarrowBarrow 1-1 Leyton Orient | Sky Bet League Two |
| 7 | 13/10/2020 | 101-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 8 | 17/10/2020 | 10 2-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 9 | 20/10/2020 | 101-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 10 | 24/10/2020 | 102-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 11 | 27/10/2020 | 101-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 12 | 31/10/2020 | 104-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 13 | 3/11/2020 | 101-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 14 | 10/11/2020 | 101-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Checkatrade Trophy Group 10 |
| 15 | 14/11/2020 | 101-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 16 | 21/11/2020 | 103-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 17 | 24/11/2020 | 101-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 18 | 28/11/2020 | 103-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 19 | 8/12/2020 | 101-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Checkatrade Trophy Second Round |
| 20 | 19/12/2020 | 101-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 21 | 26/12/2020 | 101-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
| 22 | 29/12/2020 | 102-0 v Southend UnitedLeyton Orient 2-0 Southend United | Sky Bet League Two |
| 23 | 2/1/2021 | 101-0 v Salford CityLeyton Orient 1-0 Salford City | Sky Bet League Two |
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