| 5. Round | 24/08/1999 | Middlesbrough FC | - | Leicester City | 0:3 |  |
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| 17. Round | 04/12/1999 | Bradford City | - | Middlesbrough FC | 1:1 | ||||
| 18. Round | 18/12/1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
| 19. Round | 26/12/1999 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | ||||
| 22. Round | 15/01/2000 | Middlesbrough FC | - | Derby County | 1:4 | ||||
| 21. Round | 29/01/2000 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
| 25. Round | 14/02/2000 | Middlesbrough FC | - | Aston Villa | 0:4 | ||||
| 20. Round | 19/02/2000 | Middlesbrough FC | - | Coventry City | 2:0 | ||||
| 26. Round | 26/02/2000 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
| 27. Round | 04/03/2000 | Southampton FC | - | Middlesbrough FC | 1:1 | ||||
| 28. Round | 12/03/2000 | Middlesbrough FC | - | Arsenal FC | 2:1 | ||||
| 29. Round | 18/03/2000 | Sunderland AFC | - | Middlesbrough FC | 1:1 | ||||
| 38. Round | 14/05/2000 | Everton FC | - | Middlesbrough FC | 0:2 |
England