| 24. Round | 08/02/2000 | Port Vale FC | - | Bolton Wanderers | 0:1 | ||||
| 35. Round | 07/03/2000 | Crewe Alexandra | - | Port Vale FC | 2:1 | ||||
| 36. Round | 11/03/2000 | Port Vale FC | - | Sheffield United | 2:3 | ||||
| 37. Round | 18/03/2000 | Crystal Palace | - | Port Vale FC | 1:1 | ||||
| 39. Round | 25/03/2000 | Bolton Wanderers | - | Port Vale FC | 2:1 | ||||
| 40. Round | 01/04/2000 | Port Vale FC | - | Portsmouth FC | 2:0 | ||||
| 32. Round | 04/04/2000 | Port Vale FC | - | Charlton Athletic | 2:2 | ||||
| 41. Round | 08/04/2000 | Ipswich Town | - | Port Vale FC | 3:0 | ||||
| 42. Round | 15/04/2000 | Port Vale FC | - | Barnsley FC | 2:2 | ||||
| 45. Round | 29/04/2000 | Nottingham Forest | - | Port Vale FC | 2:0 | ||||
| 46. Round | 07/05/2000 | Port Vale FC | - | Wolverhampton Wanderers | 0:1 |  |
Ireland