| 7. Jornada | 20.09.2008 | Aldershot Town | - | Gillingham FC | 2:1 | ||||
| 8. Jornada | 27.09.2008 | Gillingham FC | - | Port Vale FC | 1:0 | ||||
| 12. Jornada | 21.10.2008 | Gillingham FC | - | Notts County | 2:2 | ||||
| 16. Jornada | 15.11.2008 | Gillingham FC | - | Rotherham United | 4:0 |  |
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| 17. Jornada | 22.11.2008 | Bury FC | - | Gillingham FC | 4:0 | ||||
| 26. Jornada | 17.01.2009 | Morecambe FC | - | Gillingham FC | 0:1 | ||||
| 27. Jornada | 24.01.2009 | Gillingham FC | - | Exeter City | 1:0 |
Inglaterra