| 1. Ronde | 15.08.1998 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
| 2. Ronde | 23.08.1998 | Aston Villa | - | Middlesbrough FC | 3:1 | ||||
| 3. Ronde | 29.08.1998 | Middlesbrough FC | - | Derby County | 1:1 | ||||
| 7. Ronde | 26.09.1998 | Chelsea FC | - | Middlesbrough FC | 2:0 | ||||
| 9. Ronde | 17.10.1998 | Middlesbrough FC | - | Blackburn Rovers | 2:1 | ||||
| 10. Ronde | 24.10.1998 | Wimbledon FC | - | Middlesbrough FC | 2:2 | ||||
| 11. Ronde | 01.11.1998 | Middlesbrough FC | - | Nottingham Forest | 1:1 | ||||
| 12. Ronde | 07.11.1998 | Southampton FC | - | Middlesbrough FC | 3:3 |  |
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| 13. Ronde | 14.11.1998 | Charlton Athletic | - | Middlesbrough FC | 1:1 |  |
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| 16. Ronde | 06.12.1998 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
| 17. Ronde | 12.12.1998 | Middlesbrough FC | - | West Ham United | 1:0 | ||||
| 19. Ronde | 26.12.1998 | Middlesbrough FC | - | Liverpool FC | 1:3 | ||||
| 20. Ronde | 28.12.1998 | Derby County | - | Middlesbrough FC | 2:1 | ||||
| 23. Ronde | 30.01.1999 | Middlesbrough FC | - | Leicester City | 0:0 |  |
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| 24. Ronde | 06.02.1999 | Liverpool FC | - | Middlesbrough FC | 3:1 | |
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| 29. Ronde | 14.03.1999 | Middlesbrough FC | - | Southampton FC | 3:0 |
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