| 2. Round | 24/09/2003 | Middlesbrough FC | - | Brighton & Hove Albion | 1:0 aet |  |
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| 3. Round | 29/10/2003 | Wigan Athletic | - | Middlesbrough FC | 1:2 | ||||
| Round of 16 | 03/12/2003 | Middlesbrough FC | - | Everton FC | 5:4 pso | ||||
| Quarter-finals | 17/12/2003 | Tottenham Hotspur | - | Middlesbrough FC | 4:5 pso |  |
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| Final | 29/02/2004 | Bolton Wanderers | - | Middlesbrough FC | 1:2 | |
England