14 Oktober 2023
| 16:00 |
Chesterfield FC 
5 - 0
Kettering Town FC 
|
05 November 2023
| 13:15 |
Chesterfield FC
1 - 0
Portsmouth FC 
|
03 December 2023
| 15:00 |
Chesterfield FC
1 - 0
Leyton Orient FC 
|
06 Januari 2024
| 16:00 |
Watford FC 
2 - 1
Chesterfield FC
|