| 1. Round | 15/08/1998 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
| 2. Round | 23/08/1998 | Aston Villa | - | Middlesbrough FC | 3:1 | ||||
| 9. Round | 17/10/1998 | Middlesbrough FC | - | Blackburn Rovers | 2:1 |  |
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| 10. Round | 24/10/1998 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
| 11. Round | 01/11/1998 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 12. Round | 07/11/1998 | Southampton FC | - | Middlesbrough FC | 3:3 | ||||
| 13. Round | 14/11/1998 | Charlton Athletic | - | Middlesbrough FC | 1:1 | ||||
| 15. Round | 29/11/1998 | Arsenal FC | - | Middlesbrough FC | 1:1 | ||||
| 16. Round | 06/12/1998 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
| 19. Round | 26/12/1998 | Middlesbrough FC | - | Liverpool FC | 1:3 | ||||
| 20. Round | 28/12/1998 | Derby County | - | Middlesbrough FC | 2:1 | ||||
| 21. Round | 09/01/1999 | Middlesbrough FC | - | Aston Villa | 0:0 |  |
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| 22. Round | 16/01/1999 | Leeds United | - | Middlesbrough FC | 2:0 | |
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| 23. Round | 30/01/1999 | Middlesbrough FC | - | Leicester City | 0:0 |
England