4. Round | 03/09/1958 | Tottenham Hotspur | - | Chelsea FC | 4:0 | ||||
6. Round | 10/09/1958 | Nottingham Forest | - | Tottenham Hotspur | 1:1 | ||||
7. Round | 13/09/1958 | Arsenal FC | - | Tottenham Hotspur | 3:1 | ||||
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 |