| 1. Round | 03/08/2019 | Northampton Town | - | Walsall FC | 0:1 | ||||
| 3. Round | 17/08/2019 | Northampton Town | - | Macclesfield Town | 1:2 |  |
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| 4. Round | 20/08/2019 | Swindon Town | - | Northampton Town | 0:1 | ||||
| 5. Round | 24/08/2019 | Colchester United | - | Northampton Town | 1:0 | ||||
| 6. Round | 31/08/2019 | Northampton Town | - | Plymouth Argyle | 3:1 | ||||
| 7. Round | 07/09/2019 | Bradford City | - | Northampton Town | 2:1 | ||||
| 8. Round | 14/09/2019 | Northampton Town | - | Newport County | 2:0 | ||||
| 9. Round | 17/09/2019 | Stevenage FC | - | Northampton Town | 0:1 | |
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| 10. Round | 21/09/2019 | Northampton Town | - | Crawley Town | 2:2 |  |
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| 11. Round | 28/09/2019 | Morecambe FC | - | Northampton Town | 2:2 | ||||
| 12. Round | 05/10/2019 | Northampton Town | - | Leyton Orient | 0:1 | ||||
| 13. Round | 12/10/2019 | Scunthorpe United | - | Northampton Town | 3:0 | ||||
| 14. Round | 19/10/2019 | Northampton Town | - | Salford City | 2:0 | ||||
| 15. Round | 22/10/2019 | Carlisle United | - | Northampton Town | 0:2 | |
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| 16. Round | 26/10/2019 | Northampton Town | - | Cambridge United | 2:0 | ||||
| 21. Round | 14/12/2019 | Northampton Town | - | Forest Green Rovers | 1:0 | |
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| 23. Round | 26/12/2019 | Crawley Town | - | Northampton Town | 4:0 |
England