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
3. Round 21/08/1999 Birmingham City - Port Vale FC 4:2
4. Round 28/08/1999 Port Vale FC - Tranmere Rovers 1:0
5. Round 31/08/1999 Queens Park Rangers - Port Vale FC 3:2 yellow card
6. Round 05/09/1999 Port Vale FC - Grimsby Town 3:1
7. Round 11/09/1999 Port Vale FC - Fulham FC 0:2
8. Round 18/09/1999 Stockport County - Port Vale FC 1:0 yellow card
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 yellow card
12. Round 16/10/1999 Port Vale FC - Norwich City 0:1 yellow card
13. Round 19/10/1999 Port Vale FC - Nottingham Forest 0:2
14. Round 23/10/1999 Wolverhampton Wanderers - Port Vale FC 2:2
15. Round 26/10/1999 Swindon Town - Port Vale FC 2:1
16. Round 30/10/1999 Port Vale FC - Manchester City 1:2
17. Round 05/11/1999 Port Vale FC - Crewe Alexandra 1:0
18. Round 12/11/1999 Walsall FC - Port Vale FC 0:0
19. Round 20/11/1999 Port Vale FC - Crystal Palace 2:2
20. Round 23/11/1999 Sheffield United - Port Vale FC 1:3 red card
21. Round 27/11/1999 Charlton Athletic - Port Vale FC 2:2
22. Round 04/12/1999 Port Vale FC - Blackburn Rovers 0:0
26. Round 03/01/2000 Port Vale FC - Ipswich Town 1:2
27. Round 15/01/2000 West Bromwich Albion - Port Vale FC 0:0
28. Round 22/01/2000 Port Vale FC - Birmingham City 3:1
30. Round 05/02/2000 Port Vale FC - Queens Park Rangers 1:1
24. Round 08/02/2000 Port Vale FC - Bolton Wanderers 0:1
31. Round 12/02/2000 Grimsby Town - Port Vale FC 2:0
46. Round 07/05/2000 Port Vale FC - Wolverhampton Wanderers 0:1