| 1. Round | 10/08/1998 | York City | - | Sunderland AFC | 0:2 | ||||
| 1. Round | 17/08/1998 | Sunderland AFC | - | York City | 2:1 | ||||
| 3. Round | 26/10/1998 | Sunderland AFC | - | Grimsby Town | 2:1 aet | ||||
| Semi-finals | 25/01/1999 | Sunderland AFC | - | Leicester City | 1:2 | ||||
| Semi-finals | 16/02/1999 | Leicester City | - | Sunderland AFC | 1:1 |
England