1. Round | 21/08/2021 | Aldershot Town | - | Chesterfield FC | 0:2 | ||||
2. Round | 28/08/2021 | Chesterfield FC | - | Wealdstone FC | 2:0 | ||||
3. Round | 30/08/2021 | King's Lynn | - | Chesterfield FC | 0:2 | ||||
4. Round | 04/09/2021 | Chesterfield FC | - | Bromley FC | 2:2 | ||||
20. Round | 11/12/2021 | Grimsby Town | - | Chesterfield FC | 0:1 | ||||
22. Round | 28/12/2021 | Chesterfield FC | - | Halifax Town | 1:1 |