| 1. Round | 23/08/1958 | Bolton Wanderers | - | Leeds United | 4:0 | ||||
| 2. Round | 26/08/1958 | Leeds United | - | Luton Town | 1:1 | ||||
| 3. Round | 30/08/1958 | Leeds United | - | Burnley FC | 1:1 |  |
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| 4. Round | 03/09/1958 | Luton Town | - | Leeds United | 1:1 | ||||
| 5. Round | 06/09/1958 | Preston North End | - | Leeds United | 1:2 | ||||
| 6. Round | 10/09/1958 | Leeds United | - | Birmingham City | 0:0 | ||||
| 7. Round | 13/09/1958 | Leeds United | - | Leicester City | 1:1 | ||||
| 8. Round | 17/09/1958 | Birmingham City | - | Leeds United | 4:1 | |
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| 9. Round | 20/09/1958 | Everton FC | - | Leeds United | 3:2 | ||||
| 10. Round | 27/09/1958 | Leeds United | - | Arsenal FC | 2:1 | ||||
| 12. Round | 11/10/1958 | Portsmouth FC | - | Leeds United | 2:0 | ||||
| 13. Round | 18/10/1958 | Leeds United | - | Aston Villa | 0:0 | ||||
| 14. Round | 25/10/1958 | Tottenham Hotspur | - | Leeds United | 2:3 | ||||
| 17. Round | 15/11/1958 | Leeds United | - | Blackpool FC | 1:1 | ||||
| 18. Round | 22/11/1958 | Blackburn Rovers | - | Leeds United | 2:4 |
England