| 1er tour | 11.08.1998 | York City | - | Sunderland AFC | 0:2 | ||||
| 1er tour | 18.08.1998 | Sunderland AFC | - | York City | 2:1 | ||||
| 2e tour | 15.09.1998 | Sunderland AFC | - | Chester City | 3:0 | ||||
| 2e tour | 22.09.1998 | Chester City | - | Sunderland AFC | 0:1 | ||||
| 3e tour | 27.10.1998 | Sunderland AFC | - | Grimsby Town | 2:1 ap | ||||
| tour des 16 | 11.11.1998 | Everton FC | - | Sunderland AFC | 4:5 tab | ||||
| Quarts de finale | 01.12.1998 | Sunderland AFC | - | Luton Town | 3:0 | ||||
| Demi-finales | 26.01.1999 | Sunderland AFC | - | Leicester City | 1:2 | ||||
| Demi-finales | 17.02.1999 | Leicester City | - | Sunderland AFC | 1:1 |
Danemark
