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 | ||||
6. Round | 05/09/1999 | Port Vale FC | - | Grimsby Town | 3:1 | ||||
7. Round | 11/09/1999 | Port Vale FC | - | Fulham FC | 0:2 | ||||
9. Round | 25/09/1999 | Port Vale FC | - | Swindon Town | 2:0 |