| 1. Round | 07/08/1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
| 2. Round | 10/08/1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
| 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 |
England