Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 11.08.1998 |  | 1. Round First leg | Southend United - Gillingham FC | STH - GIL | 1:0 | 2.509 |
| 22.09.1998 | | 2. Round 2nd leg | Southend United - Coventry | STH - COV | 0:4 | 6.292 |
Roots Hall
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 11.08.1998 | | 1. Round First leg | Southend United - Gillingham FC | STH - GIL | 1:0 | 2.509 |
| 22.09.1998 | | 2. Round 2nd leg | Southend United - Coventry | STH - COV | 0:4 | 6.292 |