| League One | 20.02.07 | Carlisle United | - | Chesterfield FC | 0:0 |  |
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| League One | 07.04.07 | Chesterfield FC | - | Crewe Alexandra | 2:1 |  |
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| League Two | 02.10.07 | Wrexham FC | - | Chesterfield FC | 0:4 | |
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| League Two | 04.10.08 | Morecambe FC | - | Chesterfield FC | 2:2 | ||||
| League Two | 03.03.09 | Bury FC | - | Chesterfield FC | 1:2 | |
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