| 4. Round | 03/10/2020 | Leyton Orient | - | Cheltenham Town | 0:2 | ||||
| 3. Round | 13/10/2020 | Walsall FC | - | Leyton Orient | 2:1 | ||||
| 6. Round | 17/10/2020 | Leyton Orient | - | Grimsby Town | 2:3 |  |
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| 8. Round | 24/10/2020 | Stevenage FC | - | Leyton Orient | 0:2 | ||||
| 10. Round | 31/10/2020 | Leyton Orient | - | Bolton Wanderers | 4:0 | ||||
| 11. Round | 03/11/2020 | Forest Green Rovers | - | Leyton Orient | 2:1 |  |
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| 13. Round | 21/11/2020 | Leyton Orient | - | Harrogate Town | 3:0 | ||||
| 14. Round | 24/11/2020 | Leyton Orient | - | Bradford City | 1:0 | ||||
| 15. Round | 28/11/2020 | Port Vale FC | - | Leyton Orient | 2:3 |
England