2. Round | 14/09/1999 | Manchester City | - | Southampton FC | 0:0 | ||||
2. Round | 20/09/1999 | Southampton FC | - | Manchester City | 4:3 aet | ||||
3. Round | 12/10/1999 | Southampton FC | - | Liverpool FC | 2:1 | ||||
Round of 16 | 30/11/1999 | Aston Villa | - | Southampton FC | 4:0 |