| 4. Round | 21/08/2021 | Gillingham FC | - | Morecambe FC | 2:1 | ||||
| 5. Round | 28/08/2021 | Shrewsbury Town | - | Gillingham FC | 2:1 |  |
|||
| 7. Round | 11/09/2021 | Burton Albion | - | Gillingham FC | 1:1 | ||||
| 8. Round | 18/09/2021 | Gillingham FC | - | Milton Keynes Dons | 1:4 | ||||
| 6. Round | 21/09/2021 | Gillingham FC | - | Charlton Athletic | 1:1 | ||||
| 9. Round | 25/09/2021 | Oxford United | - | Gillingham FC | 1:1 | ||||
| 10. Round | 28/09/2021 | Cambridge United | - | Gillingham FC | 0:2 | ||||
| 11. Round | 02/10/2021 | Gillingham FC | - | Wigan Athletic | 0:2 | ||||
| 12. Round | 09/10/2021 | Wycombe Wanderers | - | Gillingham FC | 2:0 | ||||
| 14. Round | 19/10/2021 | Gillingham FC | - | Doncaster Rovers | 1:0 | ||||
| 15. Round | 23/10/2021 | Bolton Wanderers | - | Gillingham FC | 2:2 | ||||
| 17. Round | 13/11/2021 | Sheffield Wednesday | - | Gillingham FC | 1:1 | ||||
| 18. Round | 20/11/2021 | Crewe Alexandra | - | Gillingham FC | 2:0 | ||||
| 19. Round | 23/11/2021 | Gillingham FC | - | Cheltenham Town | 0:2 | ||||
| 20. Round | 27/11/2021 | Gillingham FC | - | Portsmouth FC | 0:1 |
England