| 6. Round | 28/08/1999 | Aston Villa | - | Middlesbrough FC | 1:0 | ||||
| 7. Round | 11/09/1999 | Middlesbrough FC | - | Southampton FC | 3:2 | ||||
| 15. Round | 20/11/1999 | Arsenal FC | - | Middlesbrough FC | 5:1 | ||||
| 19. Round | 26/12/1999 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | ||||
| 23. Round | 22/01/2000 | Liverpool FC | - | Middlesbrough FC | 0:0 | ||||
| 21. Round | 29/01/2000 | Manchester United | - | Middlesbrough FC | 1:0 |
Ireland