1. Round 07/08/1999 Grimsby Town - Stockport County 0:1
2. Round 14/08/1999 Stockport County - Tranmere Rovers 2:1
3. Round 21/08/1999 Portsmouth FC - Stockport County 2:0
4. Round 27/08/1999 Stockport County - Birmingham City 2:0 yellow card
7. Round 10/09/1999 Barnsley FC - Stockport County 2:1
8. Round 18/09/1999 Stockport County - Port Vale FC 1:0 Goal
9. Round 25/09/1999 Stockport County - Norwich City 2:2
5. Round 28/09/1999 Charlton Athletic - Stockport County 4:0 yellow card
10. Round 02/10/1999 Walsall FC - Stockport County 1:2
11. Round 09/10/1999 Swindon Town - Stockport County 1:1
12. Round 16/10/1999 Stockport County - Crewe Alexandra 2:1 yellow card
13. Round 19/10/1999 Stockport County - Huddersfield Town 1:1
14. Round 23/10/1999 Nottingham Forest - Stockport County 1:1
15. Round 26/10/1999 Norwich City - Stockport County 2:0
16. Round 30/10/1999 Stockport County - Walsall FC 1:1
19. Round 20/11/1999 Stockport County - Sheffield United 1:1
20. Round 23/11/1999 West Bromwich Albion - Stockport County 2:0
21. Round 27/11/1999 Blackburn Rovers - Stockport County 2:0
22. Round 04/12/1999 Stockport County - Grimsby Town 2:1
18. Round 08/12/1999 Manchester City - Stockport County 1:2 yellow card
23. Round 18/12/1999 Bolton Wanderers - Stockport County 0:1
24. Round 26/12/1999 Stockport County - Wolverhampton Wanderers 3:2
25. Round 28/12/1999 Ipswich Town - Stockport County 1:0
26. Round 03/01/2000 Stockport County - Crystal Palace 1:2
27. Round 15/01/2000 Tranmere Rovers - Stockport County 0:0
28. Round 22/01/2000 Stockport County - Portsmouth FC 1:1
29. Round 29/01/2000 Birmingham City - Stockport County 2:1
30. Round 05/02/2000 Stockport County - Charlton Athletic 1:3
31. Round 12/02/2000 Queens Park Rangers - Stockport County 1:1 yellow card
32. Round 19/02/2000 Stockport County - Blackburn Rovers 0:1
34. Round 03/03/2000 Stockport County - Barnsley FC 1:3
36. Round 11/03/2000 Stockport County - West Bromwich Albion 0:1 yellow card
40. Round 14/03/2000 Stockport County - Bolton Wanderers 0:0
37. Round 18/03/2000 Sheffield United - Stockport County 1:0
38. Round 21/03/2000 Stockport County - Manchester City 2:2
39. Round 25/03/2000 Wolverhampton Wanderers - Stockport County 2:2
41. Round 08/04/2000 Crystal Palace - Stockport County 3:3
42. Round 15/04/2000 Stockport County - Ipswich Town 0:1
43. Round 22/04/2000 Crewe Alexandra - Stockport County 3:2 yellow card
44. Round 24/04/2000 Stockport County - Swindon Town 3:0 yellow card
45. Round 29/04/2000 Huddersfield Town - Stockport County 0:2
46. Round 07/05/2000 Stockport County - Nottingham Forest 2:3 yellow card