Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 10.08.1999 |  | 1. Round First leg | Chester City - Port Vale FC | Che - PVA | 2:1 | 2.102 |
| 14.09.1999 | | 2. Round First leg | Chester City - Aston Villa | Che - AVL | 0:1 | 4.364 |
| 12.12.1999 |  | 3. Round | Chester City - Man City | Che - MCI | 1:4 | 5.469 |