| 5. Round | 06/09/1958 | Portsmouth FC | - | Chelsea FC | 2:2 | ||||
| 12. Round | 11/10/1958 | Chelsea FC | - | Bolton Wanderers | 0:1 | ||||
| 19. Round | 29/11/1958 | Everton FC | - | Chelsea FC | 3:1 | ||||
| 20. Round | 06/12/1958 | Chelsea FC | - | Birmingham City | 1:0 | ||||
| 21. Round | 13/12/1958 | West Bromwich Albion | - | Chelsea FC | 4:0 | ||||
| 32. Round | 07/03/1959 | Chelsea FC | - | Luton Town | 3:3 | ||||
| 33. Round | 14/03/1959 | Leicester City | - | Chelsea FC | 0:3 | ||||
| 34. Round | 21/03/1959 | Chelsea FC | - | Preston North End | 3:1 | ||||
| 35. Round | 27/03/1959 | Blackpool FC | - | Chelsea FC | 5:0 | ||||
| 37. Round | 30/03/1959 | Chelsea FC | - | Blackpool FC | 3:1 | ||||
| 38. Round | 04/04/1959 | Chelsea FC | - | Manchester City | 2:0 | ||||
| 39. Round | 11/04/1959 | Arsenal FC | - | Chelsea FC | 1:1 | ||||
| 29. Round | 15/04/1959 | Nottingham Forest | - | Chelsea FC | 1:3 | ||||
| 40. Round | 18/04/1959 | Chelsea FC | - | Everton FC | 3:1 | ||||
| 41. Round | 22/04/1959 | Chelsea FC | - | West Bromwich Albion | 0:2 | ||||
| 42. Round | 25/04/1959 | Birmingham City | - | Chelsea FC | 4:1 |
Ireland