| 1. Jornada | 03.08.2019 | Doncaster Rovers | - | Gillingham FC | 1:1 | ||||
| 5. Jornada | 24.08.2019 | Coventry City | - | Gillingham FC | 1:0 | ||||
| 6. Jornada | 31.08.2019 | Gillingham FC | - | Bolton Wanderers | 5:0 | ||||
| 15. Jornada | 22.10.2019 | Shrewsbury Town | - | Gillingham FC | 1:1 | ||||
| 16. Jornada | 26.10.2019 | Accrington Stanley | - | Gillingham FC | 0:1 |  |
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| 17. Jornada | 02.11.2019 | Gillingham FC | - | Rotherham United | 0:3 | ||||
| 18. Jornada | 16.11.2019 | Gillingham FC | - | Lincoln City | 1:0 | ||||
| 22. Jornada | 21.12.2019 | Gillingham FC | - | Milton Keynes Dons | 3:1 | ||||
| 24. Jornada | 29.12.2019 | Gillingham FC | - | Rochdale AFC | 1:0 | ||||
| 30. Jornada | 29.01.2020 | Gillingham FC | - | Shrewsbury Town | 2:0 | ||||
| 33. Jornada | 11.02.2020 | Blackpool FC | - | Gillingham FC | 2:3 | |
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| 34. Jornada | 15.02.2020 | Gillingham FC | - | Doncaster Rovers | 2:1 | ||||
| 26. Jornada | 18.02.2020 | Southend United | - | Gillingham FC | 0:1 | ||||
| 35. Jornada | 22.02.2020 | Lincoln City | - | Gillingham FC | 0:0 | ||||
| 36. Jornada | 29.02.2020 | Gillingham FC | - | AFC Wimbledon | 1:2 | |
Inglaterra