 |
 |
| League Two | 09/08/2003 | Southend United | - | Cheltenham Town | 2:0 | 4.403 |
| League Cup | 12/08/2003 | Southend United | - | Swindon Town | 2:3 | 3.385 |
| League Two | 23/08/2003 | Southend United | - | Mansfield Town | 0:3 | 3.837 |
| League Two | 30/08/2003 | Southend United | - | Bury FC | 1:0 | 3.172 |
| League Two | 16/09/2003 | Southend United | - | Lincoln City | 0:2 | 2.874 |
| League Two | 20/09/2003 | Southend United | - | Carlisle United | 2:2 | 4.620 |
| League Two | 04/10/2003 | Southend United | - | Huddersfield Town | 1:2 | 4.205 |
| League Two | 18/10/2003 | Southend United | - | Leyton Orient | 1:2 | 6.077 |
| League Two | 21/10/2003 | Southend United | - | Boston United | 0:2 | 2.463 |
| League Two | 01/11/2003 | Southend United | - | Northampton Town | 0:1 | 5.085 |
| League Two | 22/11/2003 | Southend United | - | Rochdale AFC | 4:0 | 3.169 |
| FA Cup | 06/12/2003 | Southend United | - | Lincoln City | 3:0 | 4.258 |
| League Two | 20/12/2003 | Southend United | - | Bristol Rovers | 0:1 | 3.771 |
| League Two | 28/12/2003 | Southend United | - | Oxford United | 0:1 | 6.449 |
England