| 8. Jornada | 18.09.1999 | Stockport County | - | Port Vale FC | 1:0 | ||||
| 9. Jornada | 25.09.1999 | Port Vale FC | - | Swindon Town | 2:0 | ||||
| 10. Jornada | 02.10.1999 | Manchester City | - | Port Vale FC | 2:1 | ||||
| 11. Jornada | 09.10.1999 | Huddersfield Town | - | Port Vale FC | 2:2 | ||||
| 31. Jornada | 12.02.2000 | Grimsby Town | - | Port Vale FC | 2:0 | ||||
| 33. Jornada | 26.02.2000 | Port Vale FC | - | Stockport County | 1:1 | ||||
| 34. Jornada | 04.03.2000 | Fulham FC | - | Port Vale FC | 3:1 | ||||
| 35. Jornada | 07.03.2000 | Crewe Alexandra | - | Port Vale FC | 2:1 | ||||
| 36. Jornada | 11.03.2000 | Port Vale FC | - | Sheffield United | 2:3 |
Inglaterra