| 1 | Tue 15 Sep 2020 | 443-2 v Plymouth ArgyleLeyton Orient 3-2 Plymouth Argyle | Carabao Cup Second Round |
| 2 | Sat 3 Oct 2020 | 440-2 v Cheltenham TownLeyton Orient 0-2 Cheltenham Town | Sky Bet League Two |
| 3 | Tue 6 Oct 2020 | 442-0 v AFC WimbledonLeyton Orient 2-0 AFC Wimbledon | Papa John’s Trophy Group 10 |
| 4 | Tue 13 Oct 2020 | 441-2 v WalsallWalsall 2-1 Leyton Orient | Sky Bet League Two |
| 5 | Sat 17 Oct 2020 | 44 2-3 v Grimsby TownLeyton Orient 2-3 Grimsby Town | Sky Bet League Two |
| 6 | Sat 24 Oct 2020 | 442-0 v StevenageStevenage 0-2 Leyton Orient | Sky Bet League Two |
| 7 | Sat 31 Oct 2020 | 444-0 v Bolton WanderersLeyton Orient 4-0 Bolton Wanderers | Sky Bet League Two |
| 8 | Tue 3 Nov 2020 | 441-2 v Forest Green RoversForest Green Rovers 2-1 Leyton Orient | Sky Bet League Two |
| 9 | Tue 10 Nov 2020 | 44 1-3 v Charlton AthleticCharlton Athletic 3-1 Leyton Orient | Papa John’s Trophy Group 10 |
| 10 | Sat 21 Nov 2020 | 443-0 v Harrogate TownLeyton Orient 3-0 Harrogate Town | Sky Bet League Two |
| 11 | Tue 24 Nov 2020 | 441-0 v Bradford CityLeyton Orient 1-0 Bradford City | Sky Bet League Two |
| 12 | Sat 28 Nov 2020 | 443-2 v Port ValePort Vale 2-3 Leyton Orient | Sky Bet League Two |
| 13 | Tue 8 Dec 2020 | 441-2 v Bristol RoversLeyton Orient 1-2 Bristol Rovers | Papa John’s Trophy Second Round |
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