| 1. Round | 22/08/1986 | Aston Villa | - | Tottenham Hotspur | 0:3 | ||||
| 2. Round | 24/08/1986 | Tottenham Hotspur | - | Newcastle United | 1:1 | ||||
| 4. Round | 01/09/1986 | Southampton FC | - | Tottenham Hotspur | 2:0 | ||||
| 5. Round | 05/09/1986 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
| 6. Round | 12/09/1986 | Tottenham Hotspur | - | Chelsea FC | 1:3 | ||||
| 8. Round | 26/09/1986 | Tottenham Hotspur | - | Everton FC | 2:0 |
England