| 4. Round | 09/09/1998 | Leicester City | - | Middlesbrough FC | 0:1 | ||||
| 8. Round | 03/10/1998 | Middlesbrough FC | - | Sheffield Wednesday | 4:0 | ||||
| 25. Round | 17/02/1999 | Everton FC | - | Middlesbrough FC | 5:0 | ||||
| 26. Round | 20/02/1999 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 | ||||
| 29. Round | 14/03/1999 | Middlesbrough FC | - | Southampton FC | 3:0 | ||||
| 37. Round | 09/05/1999 | Middlesbrough FC | - | Manchester United | 0:1 |  |
|||
| 38. Round | 16/05/1999 | West Ham United | - | Middlesbrough FC | 4:0 |
England