| 1. Round | 08/08/1997 | Middlesbrough FC | - | Charlton Athletic | 2:1 | ||||
| 1. Round | 22/08/1997 | Middlesbrough FC | - | Stoke City | 0:1 | ||||
| 1. Round | 29/08/1997 | Tranmere Rovers | - | Middlesbrough FC | 0:2 |  |
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| 2. Round | 01/09/1997 | Stockport County | - | Middlesbrough FC | 1:1 | ||||
| 3. Round | 04/10/1997 | Middlesbrough FC | - | Sheffield United | 1:2 | ||||
| 5. Round | 12/12/1997 | Middlesbrough FC | - | Reading FC | 4:0 | ||||
| 5. Round | 19/12/1997 | Manchester City | - | Middlesbrough FC | 2:0 | ||||
| 5. Round | 25/12/1997 | Huddersfield Town | - | Middlesbrough FC | 0:1 | ||||
| 5. Round | 27/12/1997 | Middlesbrough FC | - | Stockport County | 3:1 | ||||
| 7. Round | 13/02/1998 | Middlesbrough FC | - | Bradford City | 1:0 |
England