| 2. Round | 17/09/1996 | Middlesbrough FC | - | Hereford United | 7:0 | ||||
| 2. Round | 23/09/1996 | Hereford United | - | Middlesbrough FC | 0:3 |  |
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| 3. Round | 22/10/1996 | Middlesbrough FC | - | Huddersfield Town | 5:1 | ||||
| Round of 16 | 26/11/1996 | Middlesbrough FC | - | Newcastle United | 3:1 | ||||
| Quarter-finals | 07/01/1997 | Middlesbrough FC | - | Liverpool FC | 2:1 | ||||
| Semi-finals | 26/02/1997 | Stockport County | - | Middlesbrough FC | 0:2 |  |
England