| 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 | ||||
| 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 | ||||
| 24. Round | 10/02/2009 | Exeter City | - | Macclesfield Town | 4:0 | ||||
| 33. Round | 21/02/2009 | Gillingham FC | - | Macclesfield Town | 3:1 | ||||
| 25. Round | 25/02/2009 | Macclesfield Town | - | Port Vale FC | 0:2 | ||||
| 41. Round | 04/04/2009 | Macclesfield Town | - | Chesterfield FC | 1:1 | ||||
| 42. Round | 11/04/2009 | Chester City | - | Macclesfield Town | 0:2 | ||||
| 43. Round | 13/04/2009 | Macclesfield Town | - | Morecambe FC | 0:1 | ||||
| 44. Round | 18/04/2009 | Bury FC | - | Macclesfield Town | 3:0 | |
|||
| 46. Round | 02/05/2009 | Grimsby Town | - | Macclesfield Town | 0:0 |
England