| 1. Round | 09/08/2014 | Accrington Stanley | - | Southend United | 0:1 | ||||
| 2. Round | 16/08/2014 | Southend United | - | Stevenage FC | 2:0 |  |
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| 3. Round | 19/08/2014 | Southend United | - | AFC Wimbledon | 0:1 | ||||
| 4. Round | 23/08/2014 | Carlisle United | - | Southend United | 1:1 |  |
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| 5. Round | 30/08/2014 | Plymouth Argyle | - | Southend United | 2:0 | ||||
| 6. Round | 06/09/2014 | Southend United | - | Oxford United | 1:1 | ||||
| 8. Round | 16/09/2014 | Cheltenham Town | - | Southend United | 0:1 | |
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| 9. Round | 20/09/2014 | York City | - | Southend United | 2:3 | ||||
| 10. Round | 27/09/2014 | Southend United | - | Shrewsbury Town | 1:0 | ||||
| 11. Round | 04/10/2014 | Southend United | - | Morecambe FC | 0:1 | ||||
| 12. Round | 11/10/2014 | Luton Town | - | Southend United | 2:0 | |
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| 18. Round | 22/11/2014 | Tranmere Rovers | - | Southend United | 1:2 |
Ireland