| 16. Ronde | 24.10.1998 | Barnsley FC | - | Portsmouth FC | 2:1 | ||||
| 18. Ronde | 07.11.1998 | Crystal Palace | - | Portsmouth FC | 4:1 | ||||
| 17. Ronde | 10.11.1998 | Portsmouth FC | - | Norwich City | 1:2 | ||||
| 19. Ronde | 14.11.1998 | Grimsby Town | - | Portsmouth FC | 1:1 |  |
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| 20. Ronde | 21.11.1998 | Portsmouth FC | - | West Bromwich Albion | 2:1 | |
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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 | ||||
| 38. Ronde | 20.03.1999 | Norwich City | - | Portsmouth FC | 0:0 | |
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| 43. Ronde | 17.04.1999 | West Bromwich Albion | - | Portsmouth FC | 2:2 | ||||
| 46. Ronde | 09.05.1999 | Portsmouth FC | - | Bolton Wanderers | 0:2 |
Engeland
Noord-Ierland