8. Round | 18/09/1999 | Southampton FC | - | Arsenal FC | 0:1 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 | ||||
12. Round | 23/10/1999 | Southampton FC | - | Liverpool FC | 1:1 | ||||
13. Round | 30/10/1999 | Wimbledon FC | - | Southampton FC | 1:1 | ||||
14. Round | 06/11/1999 | Aston Villa | - | Southampton FC | 0:1 | ||||
15. Round | 20/11/1999 | Southampton FC | - | Tottenham Hotspur | 0:1 | ||||
16. Round | 28/11/1999 | Leeds United | - | Southampton FC | 1:0 | ||||
17. Round | 04/12/1999 | Southampton FC | - | Coventry City | 0:0 | ||||
18. Round | 18/12/1999 | Sunderland AFC | - | Southampton FC | 2:0 | ||||
19. Round | 26/12/1999 | Southampton FC | - | Chelsea FC | 1:2 | ||||
20. Round | 28/12/1999 | Watford FC | - | Southampton FC | 3:2 | ||||
22. Round | 16/01/2000 | Newcastle United | - | Southampton FC | 5:0 | ||||
23. Round | 22/01/2000 | Southampton FC | - | Everton FC | 2:0 | ||||
26. Round | 26/02/2000 | Arsenal FC | - | Southampton FC | 3:1 | ||||
33. Round | 15/04/2000 | Southampton FC | - | Watford FC | 2:0 | ||||
35. Round | 24/04/2000 | Derby County | - | Southampton FC | 2:0 |