| 2. Round | 02/09/1988 | Newcastle United | - | Tottenham Hotspur | 2:2 | ||||
| 3. Round | 09/09/1988 | Tottenham Hotspur | - | Arsenal FC | 2:3 | ||||
| 5. Round | 23/09/1988 | Tottenham Hotspur | - | Middlesbrough FC | 3:2 | ||||
| 11. Round | 04/11/1988 | Tottenham Hotspur | - | Derby County | 1:3 | ||||
| 12. Round | 11/11/1988 | Tottenham Hotspur | - | Wimbledon FC | 3:2 | ||||
| 13. Round | 19/11/1988 | Sheffield Wednesday | - | Tottenham Hotspur | 0:2 | ||||
| 1. Round | 22/11/1988 | Tottenham Hotspur | - | Coventry City | 1:1 | ||||
| 18. Round | 25/12/1988 | Tottenham Hotspur | - | Luton Town | 0:0 |
England