| 2. Runde | 20.09.1995 | Middlesbrough FC | - | Rotherham United | 2:1 |  |
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| 2. Runde | 03.10.1995 | Rotherham United | - | Middlesbrough FC | 0:1 | ||||
| 3. Runde | 25.10.1995 | Crystal Palace | - | Middlesbrough FC | 2:2 | ||||
| 3. Runde | 08.11.1995 | Middlesbrough FC | - | Crystal Palace | 2:0 | |
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| Achtelfinale | 29.11.1995 | Middlesbrough FC | - | Birmingham City | 0:0 | ||||
| Achtelfinale | 20.12.1995 | Birmingham City | - | Middlesbrough FC | 2:0 |
Norwegen