| 1. Round | 07/08/1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
| 2. Round | 10/08/1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 |  |
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| 3. Round | 14/08/1999 | Derby County | - | Middlesbrough FC | 1:3 | ||||
| 4. Round | 21/08/1999 | Middlesbrough FC | - | Liverpool FC | 1:0 | |
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| 6. Round | 28/08/1999 | Aston Villa | - | Middlesbrough FC | 1:0 | ||||
| 7. Round | 11/09/1999 | Middlesbrough FC | - | Southampton FC | 3:2 | ||||
| 12. Round | 24/10/1999 | Watford FC | - | Middlesbrough FC | 1:3 | ||||
| 13. Round | 30/10/1999 | Middlesbrough FC | - | Everton FC | 2:1 | ||||
| 14. Round | 06/11/1999 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
| 16. Round | 27/11/1999 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
| 17. Round | 04/12/1999 | Bradford City | - | Middlesbrough FC | 1:1 | |
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| 19. Round | 26/12/1999 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | |
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| 25. Round | 14/02/2000 | Middlesbrough FC | - | Aston Villa | 0:4 | ||||
| 33. Round | 15/04/2000 | Coventry City | - | Middlesbrough FC | 2:1 | ||||
| 36. Round | 29/04/2000 | West Ham United | - | Middlesbrough FC | 0:1 | |
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| 38. Round | 14/05/2000 | Everton FC | - | Middlesbrough FC | 0:2 | |
England