| N | Torneo | Jornada | Fecha | Local | Result. | Visita | Estadio | Arbitro | Público | Fuente | Obs |
|---|---|---|---|---|---|---|---|---|---|---|---|
| 1 | FA Cup 2008/09 | First Round Proper - 1 | 08/11/2008 | AFC Telford United | 2 - 2 | Southend United | [33] | ||||
| 2 | FA Cup 2008/09 | First Round Proper - 2 | 18/11/2008 | Southend United | 2 - 0 | AFC Telford United | [33] | ||||
| 3 | FA Cup 2008/09 | Second Round Proper - 1 | 29/11/2008 | Southend United | 3 - 1 | Luton Town | [33] | ||||
| 4 | FA Cup 2008/09 | Third Round Proper - 1 | 03/01/2009 | Chelsea | 1 - 1 | Southend United | [33] | ||||
| 5 | FA Cup 2008/09 | Third Round Proper - 2 | 14/01/2009 | Southend United | 1 - 4 | Chelsea | [33] |
