| 1. Round | 07/08/2010 | Southend United | - | Stockport County | 1:1 | ||||
| 2. Round | 14/08/2010 | Aldershot Town | - | Southend United | 1:0 | ||||
| 3. Round | 21/08/2010 | Southend United | - | Port Vale FC | 1:3 |  |
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| 4. Round | 27/08/2010 | Bradford City | - | Southend United | 0:2 | ||||
| 5. Round | 04/09/2010 | Southend United | - | Torquay United | 2:1 | ||||
| 6. Round | 11/09/2010 | Northampton Town | - | Southend United | 2:1 | ||||
| 11. Round | 09/10/2010 | Chesterfield FC | - | Southend United | 2:1 | ||||
| 12. Round | 16/10/2010 | Southend United | - | Crewe Alexandra | 0:2 | ||||
| 24. Round | 01/01/2011 | Oxford United | - | Southend United | 0:2 | ||||
| 25. Round | 03/01/2011 | Southend United | - | Cheltenham Town | 1:2 | ||||
| 26. Round | 08/01/2011 | Southend United | - | Chesterfield FC | 2:3 |
Scotland