| 1. Round | 05/08/2017 | Doncaster Rovers | - | Gillingham FC | 0:0 | ||||
| 4. Round | 26/08/2017 | Gillingham FC | - | Southend United | 3:3 | ||||
| 5. Round | 02/09/2017 | Gillingham FC | - | Shrewsbury Town | 1:2 | ||||
| 9. Round | 23/09/2017 | Rochdale AFC | - | Gillingham FC | 3:0 | ||||
| 12. Round | 08/10/2017 | Gillingham FC | - | Portsmouth FC | 0:1 | ||||
| 13. Round | 14/10/2017 | Peterborough United | - | Gillingham FC | 0:1 | ||||
| 14. Round | 17/10/2017 | Gillingham FC | - | Wigan Athletic | 1:1 | ||||
| 15. Round | 21/10/2017 | Gillingham FC | - | Northampton Town | 1:2 | ||||
| 16. Round | 28/10/2017 | Rotherham United | - | Gillingham FC | 1:3 |
England