| 2. Round | 19/09/2020 | Wigan Athletic | - | Gillingham FC | 2:3 |  |
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| 3. Round | 26/09/2020 | Gillingham FC | - | Blackpool FC | 2:0 | ||||
| 4. Round | 03/10/2020 | Shrewsbury Town | - | Gillingham FC | 1:1 | ||||
| 5. Round | 10/10/2020 | Gillingham FC | - | Oxford United | 3:1 | ||||
| 6. Round | 17/10/2020 | Milton Keynes Dons | - | Gillingham FC | 2:0 | ||||
| 7. Round | 20/10/2020 | Gillingham FC | - | Portsmouth FC | 0:2 | ||||
| 8. Round | 24/10/2020 | Gillingham FC | - | Fleetwood Town | 0:2 | ||||
| 17. Round | 12/12/2020 | Doncaster Rovers | - | Gillingham FC | 2:1 | ||||
| 18. Round | 15/12/2020 | Gillingham FC | - | Accrington Stanley | 0:2 | ||||
| 19. Round | 19/12/2020 | Rochdale AFC | - | Gillingham FC | 1:4 | ||||
| 21. Round | 29/12/2020 | Northampton Town | - | Gillingham FC | 3:1 | ||||
| 22. Round | 02/01/2021 | Plymouth Argyle | - | Gillingham FC | 1:0 |
England