| 3. Round | 07/01/2002 | Wimbledon FC | - | Middlesbrough FC | 0:0 | ||||
| 3. Round | 14/01/2002 | Middlesbrough FC | - | Wimbledon FC | 2:0 | ||||
| 4. Round | 25/01/2002 | Middlesbrough FC | - | Manchester United | 2:0 | ||||
| Round of 16 | 15/02/2002 | Middlesbrough FC | - | Blackburn Rovers | 1:0 | ||||
| Quarter-finals | 09/03/2002 | Middlesbrough FC | - | Everton FC | 3:0 | ||||
| Semi-finals | 13/04/2002 | Middlesbrough FC | - | Arsenal FC | 0:1 |  |
England