16. Round | 30/10/1999 | Stockport County | - | Walsall FC | 1:1 | ||||
17. Round | 06/11/1999 | Stockport County | - | Fulham FC | 2:1 | ||||
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 | ||||
23. Round | 18/12/1999 | Bolton Wanderers | - | Stockport County | 0:1 | ||||
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 | ||||
36. Round | 11/03/2000 | Stockport County | - | West Bromwich Albion | 0:1 |