1. Round | 18/08/1989 | Southampton FC | - | Millwall FC | 1:2 | ||||
2. Round | 22/08/1989 | Manchester City | - | Southampton FC | 1:2 | ||||
3. Round | 25/08/1989 | Everton FC | - | Southampton FC | 3:0 | ||||
4. Round | 28/08/1989 | Southampton FC | - | Aston Villa | 2:1 | ||||
5. Round | 08/09/1989 | Norwich City | - | Southampton FC | 4:4 | ||||
6. Round | 15/09/1989 | Southampton FC | - | Crystal Palace | 1:1 | ||||
7. Round | 22/09/1989 | Derby County | - | Southampton FC | 0:1 | ||||
8. Round | 30/09/1989 | Southampton FC | - | Wimbledon FC | 2:2 | ||||
18. Round | 16/12/1989 | Nottingham Forest | - | Southampton FC | 2:0 |