| 1. Round | 10/08/1968 | Southampton FC | - | Leeds United | 1:3 | ||||
| 2. Round | 14/08/1968 | Southampton FC | - | Liverpool FC | 2:0 | ||||
| 3. Round | 17/08/1968 | Sunderland AFC | - | Southampton FC | 1:0 | ||||
| 4. Round | 20/08/1968 | Burnley FC | - | Southampton FC | 3:1 | ||||
| 11. Round | 28/09/1968 | Queens Park Rangers | - | Southampton FC | 1:1 | ||||
| 12. Round | 05/10/1968 | West Ham United | - | Southampton FC | 0:0 | ||||
| 13. Round | 09/10/1968 | Stoke City | - | Southampton FC | 1:0 | ||||
| 14. Round | 12/10/1968 | Southampton FC | - | Everton FC | 2:5 | ||||
| 22. Round | 07/12/1968 | Southampton FC | - | Nottingham Forest | 1:1 | ||||
| 38. Round | 07/04/1969 | Southampton FC | - | Burnley FC | 5:1 | ||||
| 42. Round | 19/04/1969 | Southampton FC | - | Manchester City | 3:0 | ||||
| 41. Round | 22/04/1969 | Tottenham Hotspur | - | Southampton FC | 2:1 |
Scotland