| 8. Round | 14/09/1959 | Blackpool FC | - | Leicester City | 3:3 | ||||
| 9. Round | 19/09/1959 | Birmingham City | - | Leicester City | 3:4 | ||||
| 10. Round | 26/09/1959 | Leicester City | - | Tottenham Hotspur | 1:1 | ||||
| 11. Round | 03/10/1959 | Manchester United | - | Leicester City | 4:1 | ||||
| 12. Round | 10/10/1959 | Leicester City | - | Blackburn Rovers | 2:3 | ||||
| 13. Round | 17/10/1959 | Manchester City | - | Leicester City | 3:2 | ||||
| 14. Round | 24/10/1959 | Leicester City | - | Arsenal FC | 2:2 | ||||
| 30. Round | 24/02/1960 | Leicester City | - | Manchester United | 3:1 |  |
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| 31. Round | 27/02/1960 | Luton Town | - | Leicester City | 2:0 | ||||
| 32. Round | 05/03/1960 | Leicester City | - | Manchester City | 5:0 | ||||
| 33. Round | 15/03/1960 | Arsenal FC | - | Leicester City | 1:1 | ||||
| 34. Round | 19/03/1960 | Leicester City | - | Wolverhampton Wanderers | 2:1 | ||||
| 36. Round | 02/04/1960 | Leicester City | - | Nottingham Forest | 0:1 | ||||
| 35. Round | 06/04/1960 | Sheffield Wednesday | - | Leicester City | 2:2 | ||||
| 37. Round | 09/04/1960 | Fulham FC | - | Leicester City | 1:1 | ||||
| 38. Round | 15/04/1960 | Burnley FC | - | Leicester City | 1:0 | ||||
| 39. Round | 16/04/1960 | Leicester City | - | Everton FC | 3:3 | |
Scotland