| 8. Jornada | 27.09.2008 | Gillingham FC | - | Port Vale FC | 1:0 | ||||
| 9. Jornada | 04.10.2008 | Exeter City | - | Gillingham FC | 3:0 | ||||
| 10. Jornada | 11.10.2008 | Gillingham FC | - | Morecambe FC | 5:0 | ||||
| 12. Jornada | 21.10.2008 | Gillingham FC | - | Notts County | 2:2 | ||||
| 13. Jornada | 25.10.2008 | Gillingham FC | - | Chester City | 2:0 | ||||
| 14. Jornada | 28.10.2008 | Lincoln City | - | Gillingham FC | 2:0 | ||||
| 15. Jornada | 01.11.2008 | Macclesfield Town | - | Gillingham FC | 0:1 | ||||
| 16. Jornada | 15.11.2008 | Gillingham FC | - | Rotherham United | 4:0 | ||||
| 17. Jornada | 22.11.2008 | Bury FC | - | Gillingham FC | 4:0 | ||||
| 18. Jornada | 25.11.2008 | Gillingham FC | - | Rochdale AFC | 1:1 | ||||
| 19. Jornada | 06.12.2008 | Gillingham FC | - | Chesterfield FC | 2:1 | ||||
| 20. Jornada | 13.12.2008 | Barnet FC | - | Gillingham FC | 2:2 | ||||
| 21. Jornada | 20.12.2008 | Gillingham FC | - | Brentford FC | 1:1 | ||||
| 22. Jornada | 26.12.2008 | Dagenham & Redbridge | - | Gillingham FC | 2:0 | ||||
| 23. Jornada | 28.12.2008 | Gillingham FC | - | Wycombe Wanderers | 1:1 | ||||
| 46. Jornada | 02.05.2009 | Rochdale AFC | - | Gillingham FC | 0:1 |  |
Sierra Leona
Inglaterra