1. Round | 23/08/1958 | Manchester United | - | Chelsea FC | 5:2 | ||||
16. Round | 08/11/1958 | Chelsea FC | - | Leeds United | 2:0 | ||||
17. Round | 15/11/1958 | Manchester City | - | Chelsea FC | 5:1 | ||||
21. Round | 13/12/1958 | West Bromwich Albion | - | Chelsea FC | 4:0 | ||||
31. Round | 04/03/1959 | Bolton Wanderers | - | Chelsea FC | 6:0 | ||||
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 |