| 2. Round | 23/09/1991 | Middlesbrough FC | - | AFC Bournemouth | 1:1 | ||||
| 2. Round | 08/10/1991 | AFC Bournemouth | - | Middlesbrough FC | 1:2 aet | ||||
| 3. Round | 28/10/1991 | Middlesbrough FC | - | Barnsley FC | 1:0 | ||||
| Round of 16 | 02/12/1991 | Middlesbrough FC | - | Manchester City | 2:1 | ||||
| Quarter-finals | 07/01/1992 | Peterborough United | - | Middlesbrough FC | 0:0 | ||||
| Quarter-finals | 11/02/1992 | Middlesbrough FC | - | Peterborough United | 1:0 | ||||
| Semi-finals | 03/03/1992 | Middlesbrough FC | - | Manchester United | 0:0 | ||||
| Semi-finals | 10/03/1992 | Manchester United | - | Middlesbrough FC | 2:1 aet |
England