| 5. Round | 24/08/1968 | Southampton FC | - | Wolverhampton Wanderers | 2:1 | ||||
| 33. Round | 08/03/1969 | Southampton FC | - | Sunderland AFC | 1:0 | ||||
| 31. Round | 11/03/1969 | Nottingham Forest | - | Southampton FC | 1:0 | ||||
| 34. Round | 15/03/1969 | Wolverhampton Wanderers | - | Southampton FC | 0:0 | ||||
| 35. Round | 22/03/1969 | Southampton FC | - | Leicester City | 1:0 | ||||
| 36. Round | 29/03/1969 | Arsenal FC | - | Southampton FC | 0:0 | ||||
| 37. Round | 05/04/1969 | Southampton FC | - | Queens Park Rangers | 3:2 | ||||
| 38. Round | 07/04/1969 | Southampton FC | - | Burnley FC | 5:1 |  |
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| 40. Round | 12/04/1969 | Ipswich Town | - | Southampton FC | 0:0 | ||||
| 42. Round | 19/04/1969 | Southampton FC | - | Manchester City | 3:0 | |
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| 41. Round | 22/04/1969 | Tottenham Hotspur | - | Southampton FC | 2:1 |
England