8. Round | 18/09/1999 | Stockport County | - | Port Vale FC | 1:0 | ||||
9. Round | 25/09/1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
10. Round | 02/10/1999 | Manchester City | - | Port Vale FC | 2:1 | ||||
11. Round | 09/10/1999 | Huddersfield Town | - | Port Vale FC | 2:2 | ||||
31. Round | 12/02/2000 | Grimsby Town | - | Port Vale FC | 2:0 | ||||
33. Round | 26/02/2000 | Port Vale FC | - | Stockport County | 1:1 | ||||
34. Round | 04/03/2000 | Fulham FC | - | Port Vale FC | 3:1 | ||||
35. Round | 07/03/2000 | Crewe Alexandra | - | Port Vale FC | 2:1 | ||||
36. Round | 11/03/2000 | Port Vale FC | - | Sheffield United | 2:3 |