| 1. Round | 07/08/1998 | Port Vale FC | - | Birmingham City | 0:2 | ||||
| 2. Round | 14/08/1998 | Huddersfield Town | - | Port Vale FC | 2:1 | ||||
| 3. Round | 21/08/1998 | Port Vale FC | - | West Bromwich Albion | 0:3 | ||||
| 4. Round | 28/08/1998 | Swindon Town | - | Port Vale FC | 1:1 | ||||
| 24. Round | 18/12/1998 | Port Vale FC | - | Bury FC | 1:0 | ||||
| 28. Round | 15/01/1999 | Port Vale FC | - | Swindon Town | 0:1 | ||||
| 32. Round | 19/02/1999 | Port Vale FC | - | Crystal Palace | 1:0 |
Sweden