| 1. Round | 17/08/1998 | Sunderland AFC | - | York City | 2:1 | ||||
| 2. Round | 14/09/1998 | Sunderland AFC | - | Chester City | 3:0 | ||||
| 2. Round | 21/09/1998 | Chester City | - | Sunderland AFC | 0:1 | ||||
| Round of 16 | 10/11/1998 | Everton FC | - | Sunderland AFC | 4:5 pso | ||||
| Quarter-finals | 30/11/1998 | Sunderland AFC | - | Luton Town | 3:0 | ||||
| Semi-finals | 25/01/1999 | Sunderland AFC | - | Leicester City | 1:2 | ||||
| Semi-finals | 16/02/1999 | Leicester City | - | Sunderland AFC | 1:1 |  |
England