1. Round | 10/08/1998 | York City | - | Sunderland AFC | 0:2 | ![]() ![]() |
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2. Round | 14/09/1998 | Sunderland AFC | - | Chester City | 3:0 | ||||
2. Round | 21/09/1998 | Chester City | - | Sunderland AFC | 0:1 | ||||
3. Round | 26/10/1998 | Sunderland AFC | - | Grimsby Town | 2:1 aet | ||||
Semi-finals | 16/02/1999 | Leicester City | - | Sunderland AFC | 1:1 |