| 1. Round | 22/08/1986 | Southampton FC | - | Queens Park Rangers | 5:1 | ||||
| 2. Round | 25/08/1986 | Luton Town | - | Southampton FC | 2:1 | ||||
| 3. Round | 29/08/1986 | Norwich City | - | Southampton FC | 4:3 |  |
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| 4. Round | 01/09/1986 | Southampton FC | - | Tottenham Hotspur | 2:0 | ||||
| 5. Round | 05/09/1986 | Southampton FC | - | Nottingham Forest | 1:3 | ||||
| 6. Round | 12/09/1986 | Manchester United | - | Southampton FC | 5:1 | ||||
| 18. Round | 05/12/1986 | West Ham United | - | Southampton FC | 3:1 | ||||
| 22. Round | 26/12/1986 | Arsenal FC | - | Southampton FC | 1:0 |
England