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 | ||||
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 | ||||
10. Round | 02/10/1999 | Manchester City | - | Port Vale FC | 2:1 | ||||
12. Round | 16/10/1999 | Port Vale FC | - | Norwich City | 0:1 |