| League Two | 21.04.14 | Dagenham & Redbridge | - | Chesterfield FC | 0:1 | ||||
| Nat. League | 07.09.19 | Bromley FC | - | Chesterfield FC | 2:1 | ||||
| Nat. League | 07.12.19 | Chesterfield FC | - | Bromley FC | 1:2 | ||||
| Nat. League | 17.04.21 | Chesterfield FC | - | Bromley FC | 1:2 | ||||
| Nat. League | 27.04.21 | Bromley FC | - | Chesterfield FC | 1:2 | ||||
| Nat. League | 04.09.21 | Chesterfield FC | - | Bromley FC | 2:2 | ||||
| Nat. League | 30.04.22 | Bromley FC | - | Chesterfield FC | 4:2 | ||||
| Nat. League | 22.04.23 | Bromley FC | - | Chesterfield FC | 2:0 |  |
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| Playoffs | 07.05.23 | Chesterfield FC | - | Bromley FC | 3:2 ap |
Angleterre