| 3. Round | 21/08/1998 | Port Vale FC | - | West Bromwich Albion | 0:3 | ||||
| 5. Round | 30/08/1998 | Port Vale FC | - | Ipswich Town | 0:3 | ||||
| 9. Round | 18/09/1998 | Port Vale FC | - | Portsmouth FC | 0:2 | ||||
| 11. Round | 28/09/1998 | Bradford City | - | Port Vale FC | 4:0 | ||||
| 15. Round | 19/10/1998 | Port Vale FC | - | Crewe Alexandra | 1:0 | ||||
| 16. Round | 23/10/1998 | Watford FC | - | Port Vale FC | 2:2 | ||||
| 17. Round | 30/10/1998 | Port Vale FC | - | Sheffield United | 2:3 | ||||
| 6. Round | 03/11/1998 | Bolton Wanderers | - | Port Vale FC | 3:1 | ||||
| 18. Round | 07/11/1998 | Stockport County | - | Port Vale FC | 4:2 | ||||
| 21. Round | 27/11/1998 | Port Vale FC | - | Tranmere Rovers | 2:2 | ||||
| 23. Round | 11/12/1998 | Sunderland AFC | - | Port Vale FC | 2:0 | ||||
| 29. Round | 29/01/1999 | Ipswich Town | - | Port Vale FC | 1:0 | ||||
| 32. Round | 19/02/1999 | Port Vale FC | - | Crystal Palace | 1:0 | ||||
| 33. Round | 26/02/1999 | Portsmouth FC | - | Port Vale FC | 4:0 |
England