| 1. Ronde | 07.08.1999 | Blackburn Rovers | - | Port Vale FC | 0:0 | ||||
| 2. Ronde | 14.08.1999 | Port Vale FC | - | West Bromwich Albion | 1:2 | ||||
| 3. Ronde | 21.08.1999 | Birmingham City | - | Port Vale FC | 4:2 | ||||
| 6. Ronde | 05.09.1999 | Port Vale FC | - | Grimsby Town | 3:1 |  |
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| 7. Ronde | 11.09.1999 | Port Vale FC | - | Fulham FC | 0:2 | ||||
| 8. Ronde | 18.09.1999 | Stockport County | - | Port Vale FC | 1:0 | ||||
| 10. Ronde | 02.10.1999 | Manchester City | - | Port Vale FC | 2:1 | ||||
| 12. Ronde | 16.10.1999 | Port Vale FC | - | Norwich City | 0:1 |
Engeland