| 1. Round | 16/08/2003 | Fulham FC | - | Middlesbrough FC | 3:2 | ||||
| 2. Round | 24/08/2003 | Middlesbrough FC | - | Arsenal FC | 0:4 | ||||
| 3. Round | 26/08/2003 | Leicester City | - | Middlesbrough FC | 0:0 |  |
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| 4. Round | 30/08/2003 | Middlesbrough FC | - | Leeds United | 2:3 | ||||
| 19. Round | 28/12/2003 | Middlesbrough FC | - | Manchester United | 0:1 | ||||
| 23. Round | 31/01/2004 | Leeds United | - | Middlesbrough FC | 0:3 | ||||
| 24. Round | 07/02/2004 | Middlesbrough FC | - | Blackburn Rovers | 0:1 | ||||
| 25. Round | 11/02/2004 | Manchester United | - | Middlesbrough FC | 2:3 | ||||
| 26. Round | 21/02/2004 | Newcastle United | - | Middlesbrough FC | 2:1 | ||||
| 27. Round | 09/03/2004 | Middlesbrough FC | - | Tottenham Hotspur | 1:0 | ||||
| 28. Round | 13/03/2004 | Charlton Athletic | - | Middlesbrough FC | 1:0 | ||||
| 30. Round | 27/03/2004 | Everton FC | - | Middlesbrough FC | 1:1 | ||||
| 32. Round | 10/04/2004 | Chelsea FC | - | Middlesbrough FC | 0:0 |
England
