1. Ronde | 07.08.1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
2. Ronde | 10.08.1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
3. Ronde | 14.08.1999 | Derby County | - | Middlesbrough FC | 1:3 | ||||
27. Ronde | 04.03.2000 | Southampton FC | - | Middlesbrough FC | 1:1 |