| 1. Round | 08/08/1998 | Grimsby Town | - | Ipswich Town | 0:0 | ||||
| 2. Round | 14/08/1998 | Ipswich Town | - | Bury FC | 0:0 | ||||
| 3. Round | 21/08/1998 | Portsmouth FC | - | Ipswich Town | 0:0 | ||||
| 4. Round | 28/08/1998 | Ipswich Town | - | Sunderland AFC | 0:2 |  |
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| 5. Round | 30/08/1998 | Port Vale FC | - | Ipswich Town | 0:3 | ||||
| 7. Round | 07/09/1998 | Ipswich Town | - | Bradford City | 3:0 | ||||
| 8. Round | 11/09/1998 | Oxford United | - | Ipswich Town | 3:3 | ||||
| 9. Round | 18/09/1998 | Ipswich Town | - | Bristol City | 3:1 | ||||
| 10. Round | 25/09/1998 | Watford FC | - | Ipswich Town | 1:0 | ||||
| 11. Round | 28/09/1998 | Tranmere Rovers | - | Ipswich Town | 0:2 | ||||
| 12. Round | 02/10/1998 | Ipswich Town | - | Crystal Palace | 3:0 |  |
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| 14. Round | 16/10/1998 | Ipswich Town | - | Swindon Town | 1:0 | ||||
| 15. Round | 19/10/1998 | Ipswich Town | - | Norwich City | 0:1 | ||||
| 16. Round | 23/10/1998 | Stockport County | - | Ipswich Town | 0:1 | ||||
| 17. Round | 30/10/1998 | Ipswich Town | - | West Bromwich Albion | 2:0 | ||||
| 6. Round | 02/11/1998 | Ipswich Town | - | Wolverhampton Wanderers | 2:0 |
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