| 1. Round | 09/11/2014 | Braintree Town | - | Chesterfield FC | 0:6 |  |
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| 2. Round | 02/01/2015 | Milton Keynes Dons | - | Chesterfield FC | 0:1 | ||||
| 3. Round | 06/01/2015 | Scunthorpe United | - | Chesterfield FC | 2:2 |  |
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| 3. Round | 13/01/2015 | Chesterfield FC | - | Scunthorpe United | 2:0 aet | |
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| 4. Round | 24/01/2015 | Derby County | - | Chesterfield FC | 2:0 |
England
