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 | ||||
5. Round | 31/08/1999 | Queens Park Rangers | - | Port Vale FC | 3:2 | ||||
15. Round | 26/10/1999 | Swindon Town | - | Port Vale FC | 2:1 | ||||
16. Round | 30/10/1999 | Port Vale FC | - | Manchester City | 1:2 |