1. Round | 09/08/2008 | Shrewsbury Town | - | Macclesfield Town | 4:0 | ||||
2. Round | 16/08/2008 | Macclesfield Town | - | Bradford City | 0:2 | ||||
3. Round | 23/08/2008 | Accrington Stanley | - | Macclesfield Town | 2:0 | ||||
4. Round | 30/08/2008 | Macclesfield Town | - | Darlington FC | 0:6 | ||||
23. Round | 28/12/2008 | Macclesfield Town | - | Chester City | 3:1 | ||||
26. Round | 17/01/2009 | Aldershot Town | - | Macclesfield Town | 1:1 | ||||
27. Round | 24/01/2009 | Macclesfield Town | - | Brentford FC | 2:0 | ||||
28. Round | 27/01/2009 | Macclesfield Town | - | Wycombe Wanderers | 0:0 | ||||
29. Round | 31/01/2009 | Rotherham United | - | Macclesfield Town | 2:0 | ||||
33. Round | 21/02/2009 | Gillingham FC | - | Macclesfield Town | 3:1 | ||||
25. Round | 25/02/2009 | Macclesfield Town | - | Port Vale FC | 0:2 | ||||
34. Round | 28/02/2009 | Macclesfield Town | - | Shrewsbury Town | 3:0 | ||||
35. Round | 03/03/2009 | Bradford City | - | Macclesfield Town | 1:0 | ||||
30. Round | 31/03/2009 | Lincoln City | - | Macclesfield Town | 1:0 | ||||
46. Round | 02/05/2009 | Grimsby Town | - | Macclesfield Town | 0:0 |