| 6. Round | 05/09/2009 | Gillingham FC | - | Exeter City | 3:0 |  |
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| 7. Round | 12/09/2009 | Gillingham FC | - | Millwall FC | 2:0 | ||||
| 8. Round | 19/09/2009 | Leeds United | - | Gillingham FC | 4:1 | ||||
| 11. Round | 03/10/2009 | Southampton FC | - | Gillingham FC | 4:1 | |
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| 12. Round | 10/10/2009 | Gillingham FC | - | Wycombe Wanderers | 3:2 | ||||
| 13. Round | 17/10/2009 | Milton Keynes Dons | - | Gillingham FC | 2:0 | ||||
| 21. Round | 12/12/2009 | Huddersfield Town | - | Gillingham FC | 2:1 | ||||
| 28. Round | 23/01/2010 | Gillingham FC | - | Colchester United | 0:0 | ||||
| 25. Round | 26/01/2010 | Hartlepool United | - | Gillingham FC | 1:1 | ||||
| 29. Round | 30/01/2010 | Gillingham FC | - | Walsall FC | 0:0 | ||||
| 30. Round | 06/02/2010 | Brentford FC | - | Gillingham FC | 4:0 |  |
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| 26. Round | 09/02/2010 | Gillingham FC | - | Tranmere Rovers | 0:1 | ||||
| 46. Round | 08/05/2010 | Wycombe Wanderers | - | Gillingham FC | 3:0 |
England