| 12. Round | 05/10/1968 | Tottenham Hotspur | - | Leicester City | 3:2 | ||||
| 13. Round | 09/10/1968 | Tottenham Hotspur | - | Manchester United | 2:2 | ||||
| 14. Round | 12/10/1968 | Manchester City | - | Tottenham Hotspur | 4:0 | ||||
| 20. Round | 23/11/1968 | Southampton FC | - | Tottenham Hotspur | 2:1 | ||||
| 32. Round | 24/03/1969 | Arsenal FC | - | Tottenham Hotspur | 1:0 | ||||
| 36. Round | 29/03/1969 | Burnley FC | - | Tottenham Hotspur | 2:2 | ||||
| 37. Round | 02/04/1969 | Tottenham Hotspur | - | Newcastle United | 0:1 | ||||
| 34. Round | 12/05/1969 | Sheffield Wednesday | - | Tottenham Hotspur | 0:0 |
England