| 1. Round | 12/09/2020 | Gillingham FC | - | Hull City | 0:2 | ||||
| 2. Round | 19/09/2020 | Wigan Athletic | - | Gillingham FC | 2:3 | ||||
| 8. Round | 24/10/2020 | Gillingham FC | - | Fleetwood Town | 0:2 | ||||
| 11. Round | 03/11/2020 | Crewe Alexandra | - | Gillingham FC | 0:1 | ||||
| 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 | ||||
| 23. Round | 09/01/2021 | Gillingham FC | - | Burton Albion | 0:1 | ||||
| 25. Round | 23/01/2021 | Gillingham FC | - | Rochdale AFC | 2:2 | ||||
| 30. Round | 20/02/2021 | Gillingham FC | - | Bristol Rovers | 2:0 | ||||
| 35. Round | 09/03/2021 | Fleetwood Town | - | Gillingham FC | 1:0 |
England