6. Round | 28/08/1999 | Southampton FC | - | Sheffield Wednesday | 2:0 | ||||
7. Round | 11/09/1999 | Middlesbrough FC | - | Southampton FC | 3:2 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 | ||||
11. Round | 16/10/1999 | Leicester City | - | Southampton FC | 2:1 | ||||
14. Round | 06/11/1999 | Aston Villa | - | Southampton FC | 0:1 | ||||
15. Round | 20/11/1999 | Southampton FC | - | Tottenham Hotspur | 0:1 | ||||
19. Round | 26/12/1999 | Southampton FC | - | Chelsea FC | 1:2 | ||||
20. Round | 28/12/1999 | Watford FC | - | Southampton FC | 3:2 | ||||
21. Round | 03/01/2000 | Southampton FC | - | Bradford City | 1:0 | ||||
22. Round | 16/01/2000 | Newcastle United | - | Southampton FC | 5:0 | ||||
23. Round | 22/01/2000 | Southampton FC | - | Everton FC | 2:0 | ||||
24. Round | 05/02/2000 | Southampton FC | - | West Ham United | 2:1 | ||||
26. Round | 26/02/2000 | Arsenal FC | - | Southampton FC | 3:1 | ||||
27. Round | 04/03/2000 | Southampton FC | - | Middlesbrough FC | 1:1 |