| 4. Round | 28/08/1999 | Port Vale FC | - | Tranmere Rovers | 1:0 | ||||
| 5. Round | 31/08/1999 | Queens Park Rangers | - | Port Vale FC | 3:2 | ||||
| 6. Round | 05/09/1999 | Port Vale FC | - | Grimsby Town | 3:1 | ||||
| 7. Round | 11/09/1999 | Port Vale FC | - | Fulham FC | 0:2 | ||||
| 8. Round | 18/09/1999 | Stockport County | - | Port Vale FC | 1:0 |  |
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| 9. Round | 25/09/1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
| 10. Round | 02/10/1999 | Manchester City | - | Port Vale FC | 2:1 | ||||
| 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 |  |
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| 14. Round | 23/10/1999 | Wolverhampton Wanderers | - | Port Vale FC | 2:2 | ||||
| 15. Round | 26/10/1999 | Swindon Town | - | Port Vale FC | 2:1 | ||||
| 16. Round | 30/10/1999 | Port Vale FC | - | Manchester City | 1:2 | ||||
| 33. Round | 26/02/2000 | Port Vale FC | - | Stockport County | 1:1 | ||||
| 34. Round | 04/03/2000 | Fulham FC | - | Port Vale FC | 3:1 |
England