| 1. Runde | 10.11.2018 | Gillingham FC | - | Hartlepool United | 0:0 | ||||
| 1. Runde | 21.11.2018 | Hartlepool United | - | Gillingham FC | 3:4 n.V. | ||||
| 2. Runde | 02.12.2018 | Slough Town | - | Gillingham FC | 0:1 | ||||
| 3. Runde | 05.01.2019 | Gillingham FC | - | Cardiff City | 1:0 | ||||
| 4. Runde | 26.01.2019 | Swansea City | - | Gillingham FC | 4:1 |
Irland