| 1. Runde | 10.11.2018 | Gillingham FC | - | Hartlepool United | 0:0 | ||||
| 1. Runde | 21.11.2018 | Hartlepool United | - | Gillingham FC | 3:4 n.V. |  |
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| 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 |
England