| 1. Round | 17/08/2002 | Southampton FC | - | Middlesbrough FC | 0:0 | ||||
| 2. Round | 24/08/2002 | Middlesbrough FC | - | Fulham FC | 2:2 | ||||
| 3. Round | 03/09/2002 | Manchester United | - | Middlesbrough FC | 1:0 | ||||
| 5. Round | 10/09/2002 | Middlesbrough FC | - | Sunderland AFC | 3:0 | ||||
| 6. Round | 14/09/2002 | Everton FC | - | Middlesbrough FC | 2:1 | ||||
| 9. Round | 05/10/2002 | Middlesbrough FC | - | Bolton Wanderers | 2:0 | ||||
| 10. Round | 20/10/2002 | Charlton Athletic | - | Middlesbrough FC | 1:0 |  |
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| 14. Round | 16/11/2002 | Chelsea FC | - | Middlesbrough FC | 1:0 | ||||
| 15. Round | 23/11/2002 | Middlesbrough FC | - | Manchester City | 3:1 | ||||
| 16. Round | 30/11/2002 | West Bromwich Albion | - | Middlesbrough FC | 1:0 | ||||
| 17. Round | 07/12/2002 | Middlesbrough FC | - | West Ham United | 2:2 | ||||
| 18. Round | 14/12/2002 | Middlesbrough FC | - | Chelsea FC | 1:1 | ||||
| 21. Round | 28/12/2002 | Aston Villa | - | Middlesbrough FC | 1:0 | |
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| 23. Round | 11/01/2003 | Middlesbrough FC | - | Southampton FC | 2:2 |  |
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| 24. Round | 19/01/2003 | Fulham FC | - | Middlesbrough FC | 1:0 |
England