| League One | 16.01.16 | Wigan Athletic | - | Chesterfield FC | 3:1 | ||||
| League One | 12.03.16 | Chesterfield FC | - | Walsall FC | 1:4 |  |
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| League One | 18.10.16 | Chesterfield FC | - | Fleetwood Town | 0:1 | ||||
| League One | 04.02.17 | Chesterfield FC | - | Oldham Athletic | 0:1 | ||||
| League One | 14.04.17 | Chesterfield FC | - | Southend United | 0:4 | |
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| League Cup | 08.08.17 | Sheffield Wednesday | - | Chesterfield FC | 4:1 |
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