| FA Cup | 05.11.05 | Leyton Orient | - | Chesterfield FC | 0:0 | ||||
| FA Cup | 16.11.05 | Chesterfield FC | - | Leyton Orient | 1:2 | ||||
| League One | 10.03.07 | Chesterfield FC | - | Leyton Orient | 0:1 | ||||
| League Two | 08.01.11 | Southend United | - | Chesterfield FC | 2:3 |  |
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| League Two | 29.09.12 | Chesterfield FC | - | Torquay United | 1:1 |
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