| 1. Round | 03/08/2019 | Doncaster Rovers | - | Gillingham FC | 1:1 | ||||
| 5. Round | 24/08/2019 | Coventry City | - | Gillingham FC | 1:0 | ||||
| 6. Round | 31/08/2019 | Gillingham FC | - | Bolton Wanderers | 5:0 | ||||
| 15. Round | 22/10/2019 | Shrewsbury Town | - | Gillingham FC | 1:1 | ||||
| 16. Round | 26/10/2019 | Accrington Stanley | - | Gillingham FC | 0:1 |  |
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| 17. Round | 02/11/2019 | Gillingham FC | - | Rotherham United | 0:3 | ||||
| 18. Round | 16/11/2019 | Gillingham FC | - | Lincoln City | 1:0 | ||||
| 22. Round | 21/12/2019 | Gillingham FC | - | Milton Keynes Dons | 3:1 | ||||
| 24. Round | 29/12/2019 | Gillingham FC | - | Rochdale AFC | 1:0 | ||||
| 30. Round | 29/01/2020 | Gillingham FC | - | Shrewsbury Town | 2:0 | ||||
| 33. Round | 11/02/2020 | Blackpool FC | - | Gillingham FC | 2:3 | |
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| 34. Round | 15/02/2020 | Gillingham FC | - | Doncaster Rovers | 2:1 | ||||
| 26. Round | 18/02/2020 | Southend United | - | Gillingham FC | 0:1 | ||||
| 35. Round | 22/02/2020 | Lincoln City | - | Gillingham FC | 0:0 | ||||
| 36. Round | 29/02/2020 | Gillingham FC | - | AFC Wimbledon | 1:2 | |
England