| 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 | ||||
| 5. Round | 04/09/2010 | Bury FC | - | Gillingham FC | 5:4 | ||||
| 8. Round | 25/09/2010 | Gillingham FC | - | Burton Albion | 1:0 | ||||
| 12. Round | 16/10/2010 | Port Vale FC | - | Gillingham FC | 0:0 | ||||
| 14. Round | 30/10/2010 | Northampton Town | - | Gillingham FC | 2:1 | ||||
| 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 | ||||
| 23. Round | 28/12/2010 | Gillingham FC | - | Port Vale FC | 3:0 | ||||
| 24. Round | 01/01/2011 | Gillingham FC | - | Stevenage FC | 1:0 | ||||
| 26. Round | 08/01/2011 | Stockport County | - | Gillingham FC | 1:5 | ||||
| 21. Round | 25/01/2011 | Gillingham FC | - | Chesterfield FC | 0:2 | ||||
| 30. Round | 01/02/2011 | Stevenage FC | - | Gillingham FC | 2:2 | ||||
| 41. Round | 09/04/2011 | Lincoln City | - | Gillingham FC | 0:4 | ||||
| 46. Round | 07/05/2011 | Chesterfield FC | - | Gillingham FC | 3:1 |
England