| 1. Round | 08/08/2009 | Gillingham FC | - | Swindon Town | 5:0 | ||||
| 2. Round | 15/08/2009 | Tranmere Rovers | - | Gillingham FC | 4:2 | ||||
| 4. Round | 22/08/2009 | Gillingham FC | - | Hartlepool United | 0:1 | ||||
| 5. Round | 29/08/2009 | Walsall FC | - | Gillingham FC | 0:0 | ||||
| 6. Round | 05/09/2009 | Gillingham FC | - | Exeter City | 3:0 | ||||
| 11. Round | 03/10/2009 | Southampton FC | - | Gillingham FC | 4:1 | ||||
| 17. Round | 21/11/2009 | Bristol Rovers | - | Gillingham FC | 2:1 |  |
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| 19. Round | 01/12/2009 | Leyton Orient | - | Gillingham FC | 3:1 | ||||
| 20. Round | 05/12/2009 | Gillingham FC | - | Carlisle United | 0:0 | ||||
| 21. Round | 12/12/2009 | Huddersfield Town | - | Gillingham FC | 2:1 | ||||
| 22. Round | 19/12/2009 | Gillingham FC | - | Stockport County | 3:1 | ||||
| 23. Round | 26/12/2009 | Gillingham FC | - | Brentford FC | 0:1 | ||||
| 24. Round | 28/12/2009 | Exeter City | - | Gillingham FC | 1:1 | |
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| 30. Round | 06/02/2010 | Brentford FC | - | Gillingham FC | 4:0 |
England