| 1. Runde | 11.08.1998 | Rotherham United | - | Chesterfield FC | 0:1 |  |
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| 1. Runde | 18.08.1998 | Chesterfield FC | - | Rotherham United | 2:0 | ||||
| 2. Runde | 16.09.1998 | Leicester City | - | Chesterfield FC | 3:0 | |
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| 2. Runde | 22.09.1998 | Chesterfield FC | - | Leicester City | 1:3 | |
England