| 1. Round | 07/08/2010 | Southend United | - | Stockport County | 1:1 | ||||
| 2. Round | 14/08/2010 | Aldershot Town | - | Southend United | 1:0 | ||||
| 4. Round | 27/08/2010 | Bradford City | - | Southend United | 0:2 | ||||
| 5. Round | 04/09/2010 | Southend United | - | Torquay United | 2:1 |  |
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| 6. Round | 11/09/2010 | Northampton Town | - | Southend United | 2:1 | ||||
| 7. Round | 18/09/2010 | Southend United | - | Morecambe FC | 2:3 | ||||
| 8. Round | 25/09/2010 | Hereford United | - | Southend United | 1:3 | ||||
| 9. Round | 28/09/2010 | Gillingham FC | - | Southend United | 0:0 | ||||
| 10. Round | 02/10/2010 | Southend United | - | Lincoln City | 1:0 | ||||
| 11. Round | 09/10/2010 | Chesterfield FC | - | Southend United | 2:1 | ||||
| 13. Round | 23/10/2010 | Bury FC | - | Southend United | 1:0 | ||||
| 14. Round | 30/10/2010 | Southend United | - | Rotherham United | 1:0 | ||||
| 16. Round | 13/11/2010 | Southend United | - | Accrington Stanley | 1:1 | ||||
| 17. Round | 20/11/2010 | Shrewsbury Town | - | Southend United | 1:1 | ||||
| 18. Round | 23/11/2010 | Stevenage FC | - | Southend United | 1:1 | ||||
| 20. Round | 11/12/2010 | Burton Albion | - | Southend United | 3:1 | ||||
| 15. Round | 14/12/2010 | Cheltenham Town | - | Southend United | 0:2 |
England