1. Round | 05/08/2023 | Chesterfield FC | - | Dorking Wanderers | 4:3 | ||||
2. Round | 12/08/2023 | AFC Fylde | - | Chesterfield FC | 2:4 | ||||
3. Round | 15/08/2023 | Oxford City | - | Chesterfield FC | 1:2 | ||||
4. Round | 19/08/2023 | Chesterfield FC | - | Oldham Athletic | 1:1 | ||||
21. Round | 21/11/2023 | Woking FC | - | Chesterfield FC | 0:2 | ||||
24. Round | 16/12/2023 | Hartlepool United | - | Chesterfield FC | 0:1 | ||||
25. Round | 23/12/2023 | Chesterfield FC | - | Aldershot Town | 4:1 | ||||
23. Round | 16/01/2024 | Chesterfield FC | - | Altrincham FC | 2:1 | ||||
31. Round | 27/01/2024 | Chesterfield FC | - | Southend United | 3:0 | ||||
32. Round | 03/02/2024 | Eastleigh FC | - | Chesterfield FC | 1:3 | ||||
34. Round | 17/02/2024 | Bromley FC | - | Chesterfield FC | 4:3 | ||||
36. Round | 24/02/2024 | Chesterfield FC | - | Rochdale AFC | 2:2 | ||||
29. Round | 27/02/2024 | Barnet FC | - | Chesterfield FC | 0:2 | ||||
38. Round | 09/03/2024 | Chesterfield FC | - | AFC Fylde | 4:1 | ||||
39. Round | 12/03/2024 | Chesterfield FC | - | Oxford City | 2:0 | ||||
40. Round | 16/03/2024 | Oldham Athletic | - | Chesterfield FC | 2:2 | ||||
44. Round | 15/04/2024 | Gateshead FC | - | Chesterfield FC | 2:1 |