8. Round | 17/09/1958 | Newcastle United | - | Chelsea FC | 1:2 | ||||
9. Round | 20/09/1958 | West Ham United | - | Chelsea FC | 4:2 | ||||
10. Round | 27/09/1958 | Chelsea FC | - | Nottingham Forest | 4:1 | ||||
11. Round | 04/10/1958 | Burnley FC | - | Chelsea FC | 4:0 | ||||
12. Round | 11/10/1958 | Chelsea FC | - | Bolton Wanderers | 0:1 | ||||
18. Round | 22/11/1958 | Chelsea FC | - | Arsenal 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 | ||||
36. Round | 28/03/1959 | Leeds United | - | Chelsea FC | 4:0 | ||||
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 |