| 1. Round | 10/08/1998 | York City | - | Sunderland AFC | 0:2 | ||||
| 2. Round | 14/09/1998 | Sunderland AFC | - | Chester City | 3:0 |  |
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| 2. Round | 21/09/1998 | Chester City | - | Sunderland AFC | 0:1 | ||||
| 3. Round | 26/10/1998 | Sunderland AFC | - | Grimsby Town | 2:1 aet | ||||
| Round of 16 | 10/11/1998 | Everton FC | - | Sunderland AFC | 4:5 pso | ||||
| Quarter-finals | 30/11/1998 | Sunderland AFC | - | Luton Town | 3:0 |
England