| 23. Round | 26/12/2009 | Gillingham FC | - | Brentford FC | 0:1 | ||||
| 24. Round | 28/12/2009 | Exeter City | - | Gillingham FC | 1:1 | ||||
| 27. Round | 16/01/2010 | Swindon Town | - | Gillingham FC | 3:1 | ||||
| 28. Round | 23/01/2010 | Gillingham FC | - | Colchester United | 0:0 |  |
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| 25. Round | 26/01/2010 | Hartlepool United | - | Gillingham FC | 1:1 | ||||
| 29. Round | 30/01/2010 | Gillingham FC | - | Walsall FC | 0:0 | |
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| 30. Round | 06/02/2010 | Brentford FC | - | Gillingham FC | 4:0 | ||||
| 42. Round | 13/04/2010 | Gillingham FC | - | Brighton & Hove Albion | 1:1 |
England