| 1. Round | 12/09/2020 | Oldham Athletic | - | Leyton Orient | 0:1 | ||||
| 3. Round | 13/10/2020 | Walsall FC | - | Leyton Orient | 2:1 | ||||
| 6. Round | 17/10/2020 | Leyton Orient | - | Grimsby Town | 2:3 | ||||
| 11. Round | 03/11/2020 | Forest Green Rovers | - | Leyton Orient | 2:1 |  |
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| 32. Round | 27/02/2021 | Leyton Orient | - | Tranmere Rovers | 1:3 |  |
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| 33. Round | 02/03/2021 | Grimsby Town | - | Leyton Orient | 0:1 | ||||
| 34. Round | 06/03/2021 | Exeter City | - | Leyton Orient | 4:0 | |
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| 35. Round | 09/03/2021 | Leyton Orient | - | Stevenage FC | 0:0 | |
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| 36. Round | 13/03/2021 | Leyton Orient | - | Scunthorpe United | 1:1 | ||||
| 37. Round | 20/03/2021 | Newport County | - | Leyton Orient | 0:1 | ||||
| 23. Round | 23/03/2021 | Carlisle United | - | Leyton Orient | 0:1 | ||||
| 38. Round | 27/03/2021 | Leyton Orient | - | Oldham Athletic | 2:1 | ||||
| 39. Round | 02/04/2021 | Mansfield Town | - | Leyton Orient | 0:2 | ||||
| 40. Round | 05/04/2021 | Leyton Orient | - | Walsall FC | 0:0 | ||||
| 41. Round | 10/04/2021 | Cheltenham Town | - | Leyton Orient | 1:0 | |
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| 42. Round | 17/04/2021 | Leyton Orient | - | Barrow AFC | 2:0 | ||||
| 43. Round | 20/04/2021 | Leyton Orient | - | Cambridge United | 2:4 | |
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| 45. Round | 01/05/2021 | Leyton Orient | - | Carlisle United | 2:3 |
Happy birthday! 
England