| 1. Ronde | 07.08.1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
| 2. Ronde | 10.08.1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
| 3. Ronde | 14.08.1999 | Derby County | - | Middlesbrough FC | 1:3 |  |
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| 4. Ronde | 21.08.1999 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
| 5. Ronde | 24.08.1999 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
| 8. Ronde | 19.09.1999 | Leeds United | - | Middlesbrough FC | 2:0 | ||||
| 9. Ronde | 25.09.1999 | Middlesbrough FC | - | Chelsea FC | 0:1 | |
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| 10. Ronde | 03.10.1999 | Newcastle United | - | Middlesbrough FC | 2:1 | ||||
| 11. Ronde | 17.10.1999 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
| 12. Ronde | 24.10.1999 | Watford FC | - | Middlesbrough FC | 1:3 | ||||
| 13. Ronde | 30.10.1999 | Middlesbrough FC | - | Everton FC | 2:1 | ||||
| 14. Ronde | 06.11.1999 | Middlesbrough FC | - | Sunderland AFC | 1:1 | |
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| 16. Ronde | 27.11.1999 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| 18. Ronde | 18.12.1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | |
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| 24. Ronde | 05.02.2000 | Leicester City | - | Middlesbrough FC | 2:1 | ||||
| 25. Ronde | 14.02.2000 | Middlesbrough FC | - | Aston Villa | 0:4 |
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