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 | ||||
5. Round | 11/09/2021 | Dover Athletic | - | Chesterfield FC | 0:0 | ||||
8. Round | 25/09/2021 | Chesterfield FC | - | Torquay United | 2:2 | ||||
7. Round | 28/09/2021 | Woking FC | - | Chesterfield FC | 3:1 | ||||
10. Round | 05/10/2021 | Wrexham AFC | - | Chesterfield FC | 1:1 | ||||
11. Round | 09/10/2021 | Southend United | - | Chesterfield FC | 0:4 | ||||
12. Round | 23/10/2021 | Chesterfield FC | - | Boreham Wood | 2:1 | ||||
44. Round | 02/05/2022 | Chesterfield FC | - | Stockport County | 0:1 | ||||
45. Round | 07/05/2022 | Torquay United | - | Chesterfield FC | 2:0 | ||||
46. Round | 15/05/2022 | Chesterfield FC | - | Woking FC | 0:0 |