| 1 | Tue 15 Sep 2020 | 103-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Sat 19 Sep 2020 | 102-2 v Mansfield TownLeyton Orient 2-2 Mansfield Town | Sky Bet League Two |
| 3 | Sat 3 Oct 2020 | 100-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 4 | Tue 6 Oct 2020 | 102-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Papa John’s Trophy Group 10 |
| 5 | Tue 13 Oct 2020 | 101-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 6 | Sat 17 Oct 2020 | 10 2-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 7 | Tue 20 Oct 2020 | 101-0 v Tranmere RoversTranmere Rovers 0-1 Leyton Orient | Sky Bet League Two |
| 8 | Sat 24 Oct 2020 | 102-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 9 | Tue 27 Oct 2020 | 101-1 v Exeter CityLeyton Orient 1-1 Exeter City | Sky Bet League Two |
| 10 | Sat 31 Oct 2020 | 104-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 11 | Tue 10 Nov 2020 | 101-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 12 | Sat 14 Nov 2020 | 101-2 v Colchester UnitedColchester United 2-1 Leyton Orient | Sky Bet League Two |
| 13 | Sat 21 Nov 2020 | 103-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 14 | Tue 24 Nov 2020 | 101-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 15 | Tue 8 Dec 2020 | 101-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
| 16 | Sat 19 Dec 2020 | 101-2 v Crawley TownLeyton Orient 1-2 Crawley Town | Sky Bet League Two |
| 17 | Sat 26 Dec 2020 | 101-2 v Cambridge UnitedCambridge United 2-1 Leyton Orient | Sky Bet League Two |
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