| 8. Round | 27/09/2008 | Gillingham FC | - | Port Vale FC | 1:0 | ||||
| 9. Round | 04/10/2008 | Exeter City | - | Gillingham FC | 3:0 | ||||
| 10. Round | 11/10/2008 | Gillingham FC | - | Morecambe FC | 5:0 | ||||
| 12. Round | 21/10/2008 | Gillingham FC | - | Notts County | 2:2 | ||||
| 13. Round | 25/10/2008 | Gillingham FC | - | Chester City | 2:0 | ||||
| 14. Round | 28/10/2008 | Lincoln City | - | Gillingham FC | 2:0 | ||||
| 15. Round | 01/11/2008 | Macclesfield Town | - | Gillingham FC | 0:1 | ||||
| 16. Round | 15/11/2008 | Gillingham FC | - | Rotherham United | 4:0 | ||||
| 17. Round | 22/11/2008 | Bury FC | - | Gillingham FC | 4:0 | ||||
| 18. Round | 25/11/2008 | Gillingham FC | - | Rochdale AFC | 1:1 | ||||
| 19. Round | 06/12/2008 | Gillingham FC | - | Chesterfield FC | 2:1 | ||||
| 20. Round | 13/12/2008 | Barnet FC | - | Gillingham FC | 2:2 | ||||
| 21. Round | 20/12/2008 | Gillingham FC | - | Brentford FC | 1:1 | ||||
| 22. Round | 26/12/2008 | Dagenham & Redbridge | - | Gillingham FC | 2:0 | ||||
| 23. Round | 28/12/2008 | Gillingham FC | - | Wycombe Wanderers | 1:1 | ||||
| 46. Round | 02/05/2009 | Rochdale AFC | - | Gillingham FC | 0:1 |  |
Sierra Leone
England