| 33. Round | 23/02/2010 | Gillingham FC | - | Leyton Orient | 1:1 |  |
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| 34. Round | 27/02/2010 | Carlisle United | - | Gillingham FC | 2:0 | ||||
| 36. Round | 13/03/2010 | Stockport County | - | Gillingham FC | 0:0 | ||||
| 38. Round | 27/03/2010 | Gillingham FC | - | Milton Keynes Dons | 2:2 | ||||
| 39. Round | 03/04/2010 | Oldham Athletic | - | Gillingham FC | 1:0 | ||||
| 42. Round | 13/04/2010 | Gillingham FC | - | Brighton & Hove Albion | 1:1 | ||||
| 45. Round | 01/05/2010 | Gillingham FC | - | Southampton FC | 2:1 | ||||
| 46. Round | 08/05/2010 | Wycombe Wanderers | - | Gillingham FC | 3:0 |
England