| 8. Round | 18/09/1987 | West Ham United | - | Tottenham Hotspur | 0:1 | ||||
| 9. Round | 25/09/1987 | Manchester United | - | Tottenham Hotspur | 1:0 | ||||
| 15. Round | 03/11/1987 | Portsmouth FC | - | Tottenham Hotspur | 0:0 | ||||
| 21. Round | 19/12/1987 | Derby County | - | Tottenham Hotspur | 1:2 | ||||
| 22. Round | 25/12/1987 | Southampton FC | - | Tottenham Hotspur | 2:1 | ||||
| 23. Round | 27/12/1987 | Tottenham Hotspur | - | West Ham United | 2:1 | ||||
| 24. Round | 31/12/1987 | Tottenham Hotspur | - | Watford FC | 2:1 |  |
|||
| 25. Round | 01/01/1988 | Chelsea FC | - | Tottenham Hotspur | 0:0 | ||||
| 26. Round | 15/01/1988 | Tottenham Hotspur | - | Coventry City | 2:2 | ||||
| 27. Round | 22/01/1988 | Newcastle United | - | Tottenham Hotspur | 2:0 | ||||
| 35. Round | 25/03/1988 | Tottenham Hotspur | - | Nottingham Forest | 1:1 | ||||
| 36. Round | 01/04/1988 | Tottenham Hotspur | - | Portsmouth FC | 0:1 | ||||
| 37. Round | 03/04/1988 | Queens Park Rangers | - | Tottenham Hotspur | 2:0 |
England