| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 1938/39 | Third Round Proper - 1 | 11/01/1939 | Chesterfield | 1 - 1 | Southend United | [33] | ||||
| 2 | FA Cup 1938/39 | Third Round Proper - 2 | 16/01/1939 | Southend United | 4 - 3 | Chesterfield | [33] | ||||
| 3 | FA Cup 1953/54 | Second Round Proper - 1 | 12/12/1953 | Southend United | 1 - 2 | Chesterfield | [33] | ||||
| 4 | FA Cup 2001/02 | Second Round Proper - 1 | 08/12/2001 | Chesterfield | 1 - 1 | Southend United | [33] | ||||
| 5 | FA Cup 2001/02 | Second Round Proper - 2 | 18/12/2001 | Southend United | 2 - 0 | Chesterfield | [33] | ||||
| 6 | FA Cup 2013/14 | Second Round Proper - 1 | 07/12/2013 | Chesterfield | 1 - 3 | Southend United | [33] |
