| 1. Ronde | 09.08.2008 | Shrewsbury Town | - | Macclesfield Town | 4:0 |  |
|||
| 2. Ronde | 16.08.2008 | Macclesfield Town | - | Bradford City | 0:2 | ||||
| 3. Ronde | 23.08.2008 | Accrington Stanley | - | Macclesfield Town | 2:0 | ||||
| 4. Ronde | 30.08.2008 | Macclesfield Town | - | Darlington FC | 0:6 | ||||
| 23. Ronde | 28.12.2008 | Macclesfield Town | - | Chester City | 3:1 | ||||
| 26. Ronde | 17.01.2009 | Aldershot Town | - | Macclesfield Town | 1:1 | ||||
| 27. Ronde | 24.01.2009 | Macclesfield Town | - | Brentford FC | 2:0 | ||||
| 28. Ronde | 27.01.2009 | Macclesfield Town | - | Wycombe Wanderers | 0:0 | |
|||
| 29. Ronde | 31.01.2009 | Rotherham United | - | Macclesfield Town | 2:0 | |
|||
| 33. Ronde | 21.02.2009 | Gillingham FC | - | Macclesfield Town | 3:1 | ||||
| 25. Ronde | 25.02.2009 | Macclesfield Town | - | Port Vale FC | 0:2 | ||||
| 34. Ronde | 28.02.2009 | Macclesfield Town | - | Shrewsbury Town | 3:0 | ||||
| 35. Ronde | 03.03.2009 | Bradford City | - | Macclesfield Town | 1:0 | ||||
| 30. Ronde | 31.03.2009 | Lincoln City | - | Macclesfield Town | 1:0 | ||||
| 46. Ronde | 02.05.2009 | Grimsby Town | - | Macclesfield Town | 0:0 |
Engeland