| 1. Ronde | 05.08.2023 | Stockport County | - | Gillingham FC | 0:1 |  |
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| 2. Ronde | 12.08.2023 | Gillingham FC | - | Accrington Stanley | 1:0 | ||||
| 4. Ronde | 19.08.2023 | Crawley Town | - | Gillingham FC | 0:1 | ||||
| 5. Ronde | 26.08.2023 | Gillingham FC | - | Colchester United | 0:3 | ||||
| 6. Ronde | 02.09.2023 | Grimsby Town | - | Gillingham FC | 2:0 | ||||
| 7. Ronde | 09.09.2023 | Gillingham FC | - | Harrogate Town | 1:0 |  |
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| 8. Ronde | 16.09.2023 | Gillingham FC | - | Morecambe FC | 2:1 | |
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| 9. Ronde | 23.09.2023 | Doncaster Rovers | - | Gillingham FC | 2:1 | ||||
| 10. Ronde | 30.09.2023 | Gillingham FC | - | Mansfield Town | 1:1 | ||||
| 13. Ronde | 14.10.2023 | Walsall FC | - | Gillingham FC | 4:1 | ||||
| 15. Ronde | 24.10.2023 | Swindon Town | - | Gillingham FC | 0:1 | ||||
| 16. Ronde | 28.10.2023 | Gillingham FC | - | Newport County | 0:2 | ||||
| 36. Ronde | 02.03.2024 | Salford City | - | Gillingham FC | 0:2 | ||||
| 21. Ronde | 05.03.2024 | Barrow AFC | - | Gillingham FC | 2:0 |
Ierland