| 3. Round | 17/08/2019 | Colchester United | - | Cambridge United | 1:2 | ||||
| 4. Round | 20/08/2019 | Grimsby Town | - | Colchester United | 2:2 | ||||
| 5. Round | 24/08/2019 | Colchester United | - | Northampton Town | 1:0 | ||||
| 6. Round | 31/08/2019 | Oldham Athletic | - | Colchester United | 0:1 |  |
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| 7. Round | 07/09/2019 | Colchester United | - | Walsall FC | 0:0 | ||||
| 8. Round | 14/09/2019 | Forest Green Rovers | - | Colchester United | 1:0 | ||||
| 13. Round | 12/10/2019 | Crawley Town | - | Colchester United | 2:1 | ||||
| 25. Round | 01/01/2020 | Colchester United | - | Crawley Town | 1:1 | ||||
| 26. Round | 04/01/2020 | Stevenage FC | - | Colchester United | 0:0 | ||||
| 27. Round | 11/01/2020 | Morecambe FC | - | Colchester United | 1:1 | |
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| 28. Round | 18/01/2020 | Colchester United | - | Macclesfield Town | 2:1 | ||||
| 18. Round | 21/01/2020 | Colchester United | - | Bradford City | 0:0 | |
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| 29. Round | 25/01/2020 | Exeter City | - | Colchester United | 0:0 |
England