| 1. Round | 07/08/2010 | Gillingham FC | - | Cheltenham Town | 1:1 | ||||
| 2. Round | 14/08/2010 | Hereford United | - | Gillingham FC | 0:0 | ||||
| 3. Round | 21/08/2010 | Gillingham FC | - | Lincoln City | 0:1 | ||||
| 4. Round | 28/08/2010 | Morecambe FC | - | Gillingham FC | 1:1 | ||||
| 5. Round | 04/09/2010 | Bury FC | - | Gillingham FC | 5:4 |  |
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| 6. Round | 11/09/2010 | Gillingham FC | - | Shrewsbury Town | 2:0 | |
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| 7. Round | 18/09/2010 | Bradford City | - | Gillingham FC | 1:0 | ||||
| 8. Round | 25/09/2010 | Gillingham FC | - | Burton Albion | 1:0 | ||||
| 9. Round | 28/09/2010 | Gillingham FC | - | Southend United | 0:0 | ||||
| 10. Round | 02/10/2010 | Accrington Stanley | - | Gillingham FC | 7:4 | ||||
| 11. Round | 09/10/2010 | Gillingham FC | - | Stockport County | 2:1 | ||||
| 12. Round | 16/10/2010 | Port Vale FC | - | Gillingham FC | 0:0 | ||||
| 13. Round | 23/10/2010 | Gillingham FC | - | Torquay United | 1:1 | ||||
| 14. Round | 30/10/2010 | Northampton Town | - | Gillingham FC | 2:1 | |
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| 15. Round | 02/11/2010 | Gillingham FC | - | Wycombe Wanderers | 0:2 | ||||
| 16. Round | 13/11/2010 | Gillingham FC | - | Crewe Alexandra | 1:3 | ||||
| 17. Round | 20/11/2010 | Oxford United | - | Gillingham FC | 0:1 | ||||
| 18. Round | 23/11/2010 | Barnet FC | - | Gillingham FC | 1:2 |
England