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 | ||||
22. Round | 16/01/2000 | Newcastle United | - | Southampton FC | 5:0 | ||||
24. Round | 05/02/2000 | Southampton FC | - | West Ham United | 2:1 | ||||
25. Round | 12/02/2000 | Sheffield Wednesday | - | Southampton FC | 0:1 | ||||
26. Round | 26/02/2000 | Arsenal FC | - | Southampton FC | 3:1 |