| 4. Round | 01/09/2007 | Gillingham FC | - | Walsall FC | 2:1 | ||||
| 5. Round | 08/09/2007 | Southend United | - | Gillingham FC | 3:0 | ||||
| 8. Round | 29/09/2007 | Gillingham FC | - | Leeds United | 1:1 | ||||
| 9. Round | 02/10/2007 | Gillingham FC | - | Leyton Orient | 3:1 | ||||
| 10. Round | 06/10/2007 | Swindon Town | - | Gillingham FC | 5:0 | ||||
| 11. Round | 13/10/2007 | Gillingham FC | - | Millwall FC | 1:1 | ||||
| 12. Round | 20/10/2007 | Carlisle United | - | Gillingham FC | 2:0 | ||||
| 16. Round | 18/11/2007 | Yeovil Town | - | Gillingham FC | 2:1 | ||||
| 17. Round | 24/11/2007 | Gillingham FC | - | Hartlepool United | 2:1 | ||||
| 18. Round | 04/12/2007 | Crewe Alexandra | - | Gillingham FC | 2:3 | ||||
| 19. Round | 08/12/2007 | Gillingham FC | - | Port Vale FC | 1:2 | ||||
| 20. Round | 15/12/2007 | AFC Bournemouth | - | Gillingham FC | 1:0 | ||||
| 34. Round | 23/02/2008 | Gillingham FC | - | Huddersfield Town | 1:0 | ||||
| 35. Round | 01/03/2008 | Gillingham FC | - | Yeovil Town | 0:0 | ||||
| 21. Round | 04/03/2008 | Brighton & Hove Albion | - | Gillingham FC | 4:2 |  |
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| 39. Round | 22/03/2008 | Gillingham FC | - | AFC Bournemouth | 2:1 | ||||
| 40. Round | 24/03/2008 | Port Vale FC | - | Gillingham FC | 2:1 |
England