| 1. Round | 07/08/1999 | Blackburn Rovers | - | Port Vale FC | 0:0 | ||||
| 2. Round | 14/08/1999 | Port Vale FC | - | West Bromwich Albion | 1:2 | ||||
| 3. Round | 21/08/1999 | Birmingham City | - | Port Vale FC | 4:2 | ||||
| 5. Round | 31/08/1999 | Queens Park Rangers | - | Port Vale FC | 3:2 | ||||
| 8. Round | 18/09/1999 | Stockport County | - | Port Vale FC | 1:0 | ||||
| 9. Round | 25/09/1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
| 10. Round | 02/10/1999 | Manchester City | - | Port Vale FC | 2:1 |  |
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| 11. Round | 09/10/1999 | Huddersfield Town | - | Port Vale FC | 2:2 | ||||
| 12. Round | 16/10/1999 | Port Vale FC | - | Norwich City | 0:1 | ||||
| 13. Round | 19/10/1999 | Port Vale FC | - | Nottingham Forest | 0:2 | ||||
| 14. Round | 23/10/1999 | Wolverhampton Wanderers | - | Port Vale FC | 2:2 |  |
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| 15. Round | 26/10/1999 | Swindon Town | - | Port Vale FC | 2:1 |
England