| 1. Round | 23/08/1958 | Leicester City | - | Everton FC | 2:0 | ||||
| 2. Round | 25/08/1958 | Blackburn Rovers | - | Leicester City | 5:0 | ||||
| 13. Round | 18/10/1958 | Leicester City | - | Tottenham Hotspur | 3:4 | ||||
| 14. Round | 25/10/1958 | Chelsea FC | - | Leicester City | 5:2 | ||||
| 16. Round | 08/11/1958 | Portsmouth FC | - | Leicester City | 4:1 |  |
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| 17. Round | 15/11/1958 | Leicester City | - | Aston Villa | 6:3 | |
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| 18. Round | 22/11/1958 | West Ham United | - | Leicester City | 0:3 | |
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| 19. Round | 29/11/1958 | Leicester City | - | Nottingham Forest | 0:3 | ||||
| 20. Round | 06/12/1958 | Manchester United | - | Leicester City | 4:1 | ||||
| 21. Round | 13/12/1958 | Leicester City | - | Wolverhampton Wanderers | 1:0 | ||||
| 22. Round | 20/12/1958 | Everton FC | - | Leicester City | 0:1 | |
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| 23. Round | 26/12/1958 | Leicester City | - | Burnley FC | 1:1 | ||||
| 24. Round | 27/12/1958 | Burnley FC | - | Leicester City | 3:3 | ||||
| 25. Round | 03/01/1959 | Leicester City | - | Arsenal FC | 2:3 | ||||
| 27. Round | 31/01/1959 | Leicester City | - | Leeds United | 0:1 | ||||
| 32. Round | 07/03/1959 | Tottenham Hotspur | - | Leicester City | 6:0 |
England