Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 10.08.1999 |  | 1. Round First leg | Southend United - Oxford United | STH - OXF | 0:2 | 2.618 |
Roots Hall
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 10.08.1999 | | 1. Round First leg | Southend United - Oxford United | STH - OXF | 0:2 | 2.618 |