| 1. Ronde | 08.08.1998 | Portsmouth FC | - | Watford FC | 1:2 | ||||
| 2. Ronde | 15.08.1998 | Tranmere Rovers | - | Portsmouth FC | 1:1 | ||||
| 3. Ronde | 22.08.1998 | Portsmouth FC | - | Ipswich Town | 0:0 | ||||
| 14. Ronde | 17.10.1998 | Portsmouth FC | - | Wolverhampton Wanderers | 1:0 | ||||
| 15. Ronde | 20.10.1998 | Portsmouth FC | - | Bradford City | 2:4 |  |
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| 16. Ronde | 24.10.1998 | Barnsley FC | - | Portsmouth FC | 2:1 | ||||
| 18. Ronde | 07.11.1998 | Crystal Palace | - | Portsmouth FC | 4:1 | |
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| 21. Ronde | 28.11.1998 | Stockport County | - | Portsmouth FC | 2:0 | ||||
| 22. Ronde | 05.12.1998 | Portsmouth FC | - | Crewe Alexandra | 2:0 | ||||
| 23. Ronde | 13.12.1998 | Portsmouth FC | - | Grimsby Town | 0:1 | ||||
| 24. Ronde | 19.12.1998 | Bolton Wanderers | - | Portsmouth FC | 3:1 | ||||
| 25. Ronde | 26.12.1998 | Ipswich Town | - | Portsmouth FC | 3:0 | ||||
| 26. Ronde | 28.12.1998 | Portsmouth FC | - | Oxford United | 2:2 | ||||
| 27. Ronde | 09.01.1999 | Watford FC | - | Portsmouth FC | 0:0 |
Engeland