| 2. Round | 28/09/1988 | Lincoln City | - | Southampton FC | 1:1 | ||||
| 2. Round | 11/10/1988 | Southampton FC | - | Lincoln City | 3:1 | ||||
| 3. Round | 01/11/1988 | Scarborough FC | - | Southampton FC | 2:2 | ||||
| 3. Round | 21/11/1988 | Southampton FC | - | Scarborough FC | 1:0 | ||||
| Round of 16 | 28/11/1988 | Southampton FC | - | Tottenham Hotspur | 2:1 | ||||
| Quarter-finals | 18/01/1989 | Luton Town | - | Southampton FC | 1:1 | ||||
| Quarter-finals | 25/01/1989 | Southampton FC | - | Luton Town | 1:2 aet |
England