1. Round | 10/08/1998 | Rotherham United | - | Chesterfield FC | 0:1 | ||||
1. Round | 17/08/1998 | Chesterfield FC | - | Rotherham United | 2:0 | ||||
2. Round | 15/09/1998 | Leicester City | - | Chesterfield FC | 3:0 | ||||
2. Round | 21/09/1998 | Chesterfield FC | - | Leicester City | 1:3 |