5. Round | 24/08/1999 | Middlesbrough FC | - | Leicester City | 0:3 | ||||
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 | ||||
18. Round | 18/12/1999 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
19. Round | 26/12/1999 | Sheffield Wednesday | - | Middlesbrough FC | 1:0 | ||||
22. Round | 15/01/2000 | Middlesbrough FC | - | Derby County | 1:4 | ||||
33. Round | 15/04/2000 | Coventry City | - | Middlesbrough FC | 2:1 | ||||
35. Round | 02/05/2000 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
37. Round | 06/05/2000 | Middlesbrough FC | - | Watford FC | 1:1 | ||||
38. Round | 14/05/2000 | Everton FC | - | Middlesbrough FC | 0:2 |