| 1er tour | 11.08.1998 | York City | - | Sunderland AFC | 0:2 | ||||
| 1er tour | 18.08.1998 | Sunderland AFC | - | York City | 2:1 |  |
 |
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| 2e tour | 15.09.1998 | Sunderland AFC | - | Chester City | 3:0 | |
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| Demi-finales | 26.01.1999 | Sunderland AFC | - | Leicester City | 1:2 | ||||
| Demi-finales | 17.02.1999 | Leicester City | - | Sunderland AFC | 1:1 |
Angleterre