| 1. Jornada | 07.08.1999 | Portsmouth FC | - | Sheffield United | 2:0 | ||||
| 2. Jornada | 14.08.1999 | Wolverhampton Wanderers | - | Portsmouth FC | 1:1 | ||||
| 3. Jornada | 21.08.1999 | Portsmouth FC | - | Stockport County | 2:0 | ||||
| 4. Jornada | 28.08.1999 | Barnsley FC | - | Portsmouth FC | 6:0 | ||||
| 5. Jornada | 30.08.1999 | Portsmouth FC | - | Huddersfield Town | 0:0 | ||||
| 7. Jornada | 11.09.1999 | Portsmouth FC | - | Ipswich Town | 1:1 | ||||
| 8. Jornada | 18.09.1999 | Tranmere Rovers | - | Portsmouth FC | 2:4 |  |
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| 9. Jornada | 25.09.1999 | Portsmouth FC | - | Grimsby Town | 1:2 | ||||
| 10. Jornada | 02.10.1999 | Crystal Palace | - | Portsmouth FC | 4:0 | ||||
| 18. Jornada | 14.11.1999 | West Bromwich Albion | - | Portsmouth FC | 3:2 |
Francia