| 2. Round | 06/08/2022 | Gillingham FC | - | Rochdale AFC | 1:0 | ||||
| 3. Round | 13/08/2022 | Tranmere Rovers | - | Gillingham FC | 3:0 | ||||
| 4. Round | 16/08/2022 | Gillingham FC | - | Harrogate Town | 0:2 | ||||
| 5. Round | 20/08/2022 | Gillingham FC | - | Walsall FC | 0:0 | ||||
| 6. Round | 27/08/2022 | Carlisle United | - | Gillingham FC | 1:0 | ||||
| 7. Round | 03/09/2022 | Gillingham FC | - | Swindon Town | 0:0 | ||||
| 10. Round | 17/09/2022 | Gillingham FC | - | Mansfield Town | 0:2 | ||||
| 12. Round | 01/10/2022 | Gillingham FC | - | Sutton United | 1:0 | ||||
| 14. Round | 08/10/2022 | Crewe Alexandra | - | Gillingham FC | 1:1 | ||||
| 15. Round | 15/10/2022 | Gillingham FC | - | Stevenage FC | 1:1 | ||||
| 16. Round | 22/10/2022 | Gillingham FC | - | Barrow AFC | 1:1 | ||||
| 13. Round | 25/10/2022 | Leyton Orient | - | Gillingham FC | 2:0 | ||||
| 17. Round | 29/10/2022 | Doncaster Rovers | - | Gillingham FC | 1:0 | ||||
| 18. Round | 12/11/2022 | Gillingham FC | - | Northampton Town | 0:2 | ||||
| 19. Round | 19/11/2022 | Newport County | - | Gillingham FC | 2:0 |  |
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| 8. Round | 22/11/2022 | Crawley Town | - | Gillingham FC | 0:0 | ||||
| 20. Round | 03/12/2022 | Gillingham FC | - | Salford City | 0:3 |
England