| League Two | 08/01/11 | Southend United | - | Chesterfield FC | 2:3 |  |
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| League Two | 21/12/12 | Southend United | - | Chesterfield FC | 3:0 | ||||
| League Two | 26/01/13 | Chesterfield FC | - | Southend United | 0:1 | ||||
| League Two | 24/08/13 | Chesterfield FC | - | Southend United | 2:1 | ||||
| FA Cup | 07/12/13 | Chesterfield FC | - | Southend United | 1:3 | ||||
| League Two | 18/01/14 | Southend United | - | Chesterfield FC | 3:0 | |
Ireland