| 4. Jornada | 28.08.1999 | Port Vale FC | - | Tranmere Rovers | 1:0 | ||||
| 5. Jornada | 31.08.1999 | Queens Park Rangers | - | Port Vale FC | 3:2 | ||||
| 6. Jornada | 05.09.1999 | Port Vale FC | - | Grimsby Town | 3:1 | ||||
| 7. Jornada | 11.09.1999 | Port Vale FC | - | Fulham FC | 0:2 | ||||
| 8. Jornada | 18.09.1999 | Stockport County | - | Port Vale FC | 1:0 |  |
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| 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 | ||||
| 12. Jornada | 16.10.1999 | Port Vale FC | - | Norwich City | 0:1 | ||||
| 13. Jornada | 19.10.1999 | Port Vale FC | - | Nottingham Forest | 0:2 |  |
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| 14. Jornada | 23.10.1999 | Wolverhampton Wanderers | - | Port Vale FC | 2:2 | ||||
| 15. Jornada | 26.10.1999 | Swindon Town | - | Port Vale FC | 2:1 | ||||
| 16. Jornada | 30.10.1999 | Port Vale FC | - | Manchester City | 1:2 | ||||
| 33. Jornada | 26.02.2000 | Port Vale FC | - | Stockport County | 1:1 | ||||
| 34. Jornada | 04.03.2000 | Fulham FC | - | Port Vale FC | 3:1 |
Inglaterra