| 1. Journée | 09.08.1998 | Grimsby Town | - | Ipswich Town | 0:0 | ||||
| 4. Journée | 29.08.1998 | Ipswich Town | - | Sunderland AFC | 0:2 |  |
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| 5. Journée | 31.08.1998 | Port Vale FC | - | Ipswich Town | 0:3 | ||||
| 9. Journée | 19.09.1998 | Ipswich Town | - | Bristol City | 3:1 | ||||
| 11. Journée | 29.09.1998 | Tranmere Rovers | - | Ipswich Town | 0:2 | ||||
| 14. Journée | 17.10.1998 | Ipswich Town | - | Swindon Town | 1:0 | |
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| 24. Journée | 20.12.1998 | Sheffield United | - | Ipswich Town | 1:2 | ||||
| 25. Journée | 26.12.1998 | Ipswich Town | - | Portsmouth FC | 3:0 | ||||
| 26. Journée | 28.12.1998 | Wolverhampton Wanderers | - | Ipswich Town | 1:0 | ||||
| 40. Journée | 03.04.1999 | Swindon Town | - | Ipswich Town | 0:6 | ||||
| 41. Journée | 05.04.1999 | Ipswich Town | - | Queens Park Rangers | 3:1 |
Pays-Bas