Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 17.08.1999 |  | 1. Round First leg | Torquay United - Portsmouth | TQU - POR | 0:0 | 3.209 |
| 21.12.1999 |  | 3. Round Repeat | Torquay United - QPR | TQU - QPR | 2:3 | 5.232 |
Plainmoor
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 17.08.1999 | | 1. Round First leg | Torquay United - Portsmouth | TQU - POR | 0:0 | 3.209 |
| 21.12.1999 | | 3. Round Repeat | Torquay United - QPR | TQU - QPR | 2:3 | 5.232 |