| 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 | ||||
| 27. Round | 31/01/1959 | Leicester City | - | Leeds United | 0:1 | ||||
| 28. Round | 07/02/1959 | Leeds United | - | Everton FC | 1:0 | ||||
| 35. Round | 14/02/1959 | Wolverhampton Wanderers | - | Leeds United | 6:2 | ||||
| 32. Round | 07/03/1959 | Aston Villa | - | Leeds United | 2:1 | ||||
| 33. Round | 14/03/1959 | Leeds United | - | Tottenham Hotspur | 3:1 | ||||
| 34. Round | 21/03/1959 | Manchester United | - | Leeds United | 4:0 | ||||
| 36. Round | 28/03/1959 | Leeds United | - | Chelsea FC | 4:0 | ||||
| 37. Round | 31/03/1959 | Leeds United | - | Wolverhampton Wanderers | 1:3 | ||||
| 38. Round | 04/04/1959 | Blackpool FC | - | Leeds United | 3:0 | ||||
| 39. Round | 11/04/1959 | Leeds United | - | Blackburn Rovers | 2:1 | ||||
| 40. Round | 18/04/1959 | Newcastle United | - | Leeds United | 2:2 | ||||
| 41. Round | 22/04/1959 | Nottingham Forest | - | Leeds United | 0:3 |
England