1. Round | 07/08/1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
2. Round | 10/08/1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
4. Round | 21/08/1999 | Middlesbrough FC | - | Liverpool FC | 1:0 | ||||
7. Round | 11/09/1999 | Middlesbrough FC | - | Southampton FC | 3:2 | ||||
9. Round | 25/09/1999 | Middlesbrough FC | - | Chelsea FC | 0:1 | ||||
15. Round | 20/11/1999 | Arsenal FC | - | Middlesbrough FC | 5:1 | ||||
17. Round | 04/12/1999 | Bradford City | - | Middlesbrough FC | 1:1 | ||||
25. Round | 14/02/2000 | Middlesbrough FC | - | Aston Villa | 0:4 |