| League Two | 06/10/07 | Chesterfield FC | - | Macclesfield Town | 2:2 | ||||
| League Two | 26/04/08 | Macclesfield Town | - | Chesterfield FC | 1:0 | ||||
| League Two | 12/12/08 | Chesterfield FC | - | Macclesfield Town | 2:4 | ||||
| League Two | 04/04/09 | Macclesfield Town | - | Chesterfield FC | 1:1 | ||||
| League Two | 19/09/09 | Chesterfield FC | - | Macclesfield Town | 4:1 |
Scotland