1. Round | 23/08/1958 | Tottenham Hotspur | - | Blackpool FC | 2:3 | ||||
2. Round | 27/08/1958 | Chelsea FC | - | Tottenham Hotspur | 4:2 | ||||
13. Round | 18/10/1958 | Leicester City | - | Tottenham Hotspur | 3:4 | ||||
20. Round | 06/12/1958 | Tottenham Hotspur | - | Preston North End | 1:2 | ||||
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 |