| 3. Jornada | 18.08.2018 | Walsall FC | - | Gillingham FC | 2:1 | ||||
| 5. Jornada | 25.08.2018 | Gillingham FC | - | Coventry City | 1:1 | ||||
| 6. Jornada | 01.09.2018 | Barnsley FC | - | Gillingham FC | 2:1 | ||||
| 7. Jornada | 08.09.2018 | Gillingham FC | - | AFC Wimbledon | 0:1 | ||||
| 9. Jornada | 22.09.2018 | Gillingham FC | - | Peterborough United | 2:4 | ||||
| 13. Jornada | 13.10.2018 | Gillingham FC | - | Southend United | 0:2 | ||||
| 15. Jornada | 23.10.2018 | Plymouth Argyle | - | Gillingham FC | 3:1 |
Inglaterra