8. Round | 18/09/1999 | Stockport County | - | Port Vale FC | 1:0 | ||||
6. Round | 02/11/1999 | Stockport County | - | Queens Park Rangers | 3:3 | ||||
22. Round | 04/12/1999 | Stockport County | - | Grimsby Town | 2:1 | ||||
28. Round | 22/01/2000 | Stockport County | - | Portsmouth FC | 1:1 | ||||
43. Round | 22/04/2000 | Crewe Alexandra | - | Stockport County | 3:2 | ||||
44. Round | 24/04/2000 | Stockport County | - | Swindon Town | 3:0 | ||||
45. Round | 29/04/2000 | Huddersfield Town | - | Stockport County | 0:2 |