| League Two | 05/05/18 | Barnet FC | - | Chesterfield FC | 3:0 | ||||
| Nat. League | 13/08/19 | Chesterfield FC | - | Woking FC | 1:2 |  |
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| Nat. League | 10/10/20 | Chesterfield FC | - | Woking FC | 4:0 | ||||
| Nat. League | 08/05/21 | Woking FC | - | Chesterfield FC | 1:4 | ||||
| Nat. League | 28/09/21 | Woking FC | - | Chesterfield FC | 3:1 | ||||
| Nat. League | 15/05/22 | Chesterfield FC | - | Woking FC | 0:0 | ||||
| Nat. League | 07/02/23 | Chesterfield FC | - | Woking FC | 1:3 | ||||
| Nat. League | 30/09/23 | Maidenhead United | - | Chesterfield FC | 1:1 | ||||
| Nat. League | 20/04/24 | Chesterfield FC | - | Maidenhead United | 3:2 |
England