| 4. Round | 20/08/2019 | Ipswich Town | - | AFC Wimbledon | 2:1 | ||||
| 5. Round | 24/08/2019 | Bolton Wanderers | - | Ipswich Town | 0:5 | ||||
| 6. Round | 31/08/2019 | Ipswich Town | - | Shrewsbury Town | 3:0 | ||||
| 8. Round | 14/09/2019 | Ipswich Town | - | Doncaster Rovers | 0:0 | ||||
| 9. Round | 17/09/2019 | Milton Keynes Dons | - | Ipswich Town | 0:1 | ||||
| 14. Round | 20/10/2019 | Accrington Stanley | - | Ipswich Town | 2:0 | ||||
| 15. Round | 23/10/2019 | Ipswich Town | - | Rotherham United | 0:2 | ||||
| 7. Round | 05/11/2019 | Rochdale AFC | - | Ipswich Town | 0:1 | ||||
| 19. Round | 23/11/2019 | Ipswich Town | - | Blackpool FC | 2:2 | ||||
| 21. Round | 14/12/2019 | Ipswich Town | - | Bristol Rovers | 1:2 |
England