| 29. Round | 29/01/2008 | Tranmere Rovers | - | Gillingham FC | 2:0 | ||||
| 30. Round | 02/02/2008 | Gillingham FC | - | Cheltenham Town | 0:0 | ||||
| 31. Round | 09/02/2008 | Oldham Athletic | - | Gillingham FC | 2:1 |  |
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| 33. Round | 16/02/2008 | Northampton Town | - | Gillingham FC | 4:0 | ||||
| 21. Round | 04/03/2008 | Brighton & Hove Albion | - | Gillingham FC | 4:2 | ||||
| 36. Round | 08/03/2008 | Hartlepool United | - | Gillingham FC | 4:0 | |
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| 37. Round | 11/03/2008 | Doncaster Rovers | - | Gillingham FC | 2:1 | ||||
| 38. Round | 15/03/2008 | Gillingham FC | - | Crewe Alexandra | 0:3 | ||||
| 42. Round | 05/04/2008 | Millwall FC | - | Gillingham FC | 1:1 | ||||
| 43. Round | 12/04/2008 | Gillingham FC | - | Swansea City | 1:2 |
England