| 1. Round | 12/09/2020 | Oldham Athletic | - | Leyton Orient | 0:1 | ||||
| 2. Round | 19/09/2020 | Leyton Orient | - | Mansfield Town | 2:2 | ||||
| 4. Round | 03/10/2020 | Leyton Orient | - | Cheltenham Town | 0:2 | ||||
| 16. Round | 05/12/2020 | Scunthorpe United | - | Leyton Orient | 2:0 | ||||
| 17. Round | 12/12/2020 | Leyton Orient | - | Newport County | 2:1 |  |
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| 18. Round | 15/12/2020 | Morecambe FC | - | Leyton Orient | 2:1 | |
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| 19. Round | 19/12/2020 | Leyton Orient | - | Crawley Town | 1:2 | ||||
| 20. Round | 26/12/2020 | Cambridge United | - | Leyton Orient | 2:1 | ||||
| 21. Round | 29/12/2020 | Leyton Orient | - | Southend United | 2:0 | |
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| 22. Round | 02/01/2021 | Leyton Orient | - | Salford City | 1:0 | ||||
| 24. Round | 16/01/2021 | Leyton Orient | - | Morecambe FC | 2:0 |  |
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| 26. Round | 23/01/2021 | Leyton Orient | - | Forest Green Rovers | 0:1 |
England