| 4. Round | 08/09/1998 | Leeds United | - | Southampton FC | 3:0 | ||||
| 6. Round | 19/09/1998 | Southampton FC | - | Tottenham Hotspur | 1:1 | ||||
| 7. Round | 28/09/1998 | West Ham United | - | Southampton FC | 1:0 | ||||
| 8. Round | 03/10/1998 | Southampton FC | - | Manchester United | 0:3 | ||||
| 9. Round | 17/10/1998 | Arsenal FC | - | Southampton FC | 1:1 |
England