| 1. Round | 10/11/2018 | Gillingham FC | - | Hartlepool United | 0:0 | ||||
| 1. Round | 21/11/2018 | Hartlepool United | - | Gillingham FC | 3:4 aet | ||||
| 2. Round | 02/12/2018 | Slough Town | - | Gillingham FC | 0:1 | ||||
| 3. Round | 05/01/2019 | Gillingham FC | - | Cardiff City | 1:0 | ||||
| 4. Round | 26/01/2019 | Swansea City | - | Gillingham FC | 4:1 |
Ireland