| 1. Round | 16/08/1996 | Southend United | - | Tranmere Rovers | 1:1 | ||||
| 2. Round | 23/08/1996 | Oxford United | - | Southend United | 5:0 | ||||
| 20. Round | 22/11/1996 | Stoke City | - | Southend United | 1:2 | ||||
| 21. Round | 29/11/1996 | Southend United | - | Oldham Athletic | 1:1 | ||||
| 22. Round | 06/12/1996 | Barnsley FC | - | Southend United | 3:0 | ||||
| 23. Round | 13/12/1996 | Queens Park Rangers | - | Southend United | 4:0 |  |
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| 24. Round | 19/12/1996 | Southend United | - | Birmingham City | 1:1 | ||||
| 25. Round | 25/12/1996 | Southend United | - | Charlton Athletic | 0:2 | |
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| 39. Round | 21/03/1997 | Southend United | - | Oxford United | 2:2 |
England