Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 22.08.2000 |  | 1. Round First leg | Southend United - Birmingham | STH - BIR | 0:5 | 3.694 |
| 28.11.2000 |  | 1. Round Repeat | Southend United - Torquay United | STH - TQU | 2:1 | 3.877 |
| 10.12.2000 | | 2. Round | Canvey Island - Southend United | - STH | 1:2 | 11.402 |