| League Two | 17/10/17 | Crawley Town | - | Chesterfield FC | 0:2 | ||||
| Nat. League | 20/10/20 | Wealdstone FC | - | Chesterfield FC | 3:2 |  |
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| Nat. League | 15/05/21 | Chesterfield FC | - | Wealdstone FC | 0:0 | ||||
| Nat. League | 28/08/21 | Chesterfield FC | - | Wealdstone FC | 2:0 | ||||
| Nat. League | 12/03/22 | Boreham Wood | - | Chesterfield FC | 1:1 | ||||
| Nat. League | 29/10/22 | Chesterfield FC | - | Boreham Wood | 2:0 | ||||
| Nat. League | 04/02/23 | Boreham Wood | - | Chesterfield FC | 1:0 | ||||
| Nat. League | 23/01/24 | Chesterfield FC | - | Woking FC | 1:0 |
England