| 2. Round | 07/08/2018 | Chesterfield FC | - | Aldershot Town | 3:0 | ||||
| 3. Round | 11/08/2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
| 4. Round | 14/08/2018 | Barrow AFC | - | Chesterfield FC | 3:2 |
| 2. Round | 07/08/2018 | Chesterfield FC | - | Aldershot Town | 3:0 | ||||
| 3. Round | 11/08/2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
| 4. Round | 14/08/2018 | Barrow AFC | - | Chesterfield FC | 3:2 |
| Samuel Wedgbury | |
| Born: | 26.02.1989 |
| Place of birth: |
Oldbury, 
England |
| Nationality: |
England
|
| Height: | 185 cm |
| Weight: | 80 kg |
| Position(s): | Right Midfielder |
| Foot: | right |