3. Round | 30/08/1958 | Blackburn Rovers | - | Tottenham Hotspur | 5:0 | ||||
8. Round | 17/09/1958 | Tottenham Hotspur | - | Nottingham Forest | 1:0 | ||||
9. Round | 20/09/1958 | Manchester United | - | Tottenham Hotspur | 2:2 | ||||
10. Round | 27/09/1958 | Tottenham Hotspur | - | Wolverhampton Wanderers | 2:1 | ||||
11. Round | 04/10/1958 | Portsmouth FC | - | Tottenham Hotspur | 1:1 | ||||
12. Round | 11/10/1958 | Tottenham Hotspur | - | Everton FC | 10:4 | ||||
13. Round | 18/10/1958 | Leicester City | - | Tottenham Hotspur | 3:4 | ||||
14. Round | 25/10/1958 | Tottenham Hotspur | - | Leeds United | 2:3 | ||||
15. Round | 01/11/1958 | Manchester City | - | Tottenham Hotspur | 5:1 | ||||
21. Round | 13/12/1958 | Burnley FC | - | Tottenham Hotspur | 3:1 | ||||
22. Round | 20/12/1958 | Blackpool FC | - | Tottenham Hotspur | 0:0 | ||||
23. Round | 25/12/1958 | West Ham United | - | Tottenham Hotspur | 2:1 | ||||
24. Round | 26/12/1958 | Tottenham Hotspur | - | West Ham United | 1:4 | ||||
36. Round | 28/03/1959 | Bolton Wanderers | - | Tottenham Hotspur | 4:1 |